Acylated N-(1,2,5-oxadiazol-3-yl)-, N-(1,3,4-oxadiazol-2-yl)-, N-(tetrazol-5-yl)- and N-(triazol-5-yl)-aryl carboxamides, and use thereof as herbicides

ABSTRACT

In this formula (I), R, V, X, Y and Z are radicals such as hydrogen, organic radicals such as alkyl, and other radicals such as halogen. Q is an oxadiazole, triazole or tetrazole radical. W is CY or N.

The invention relates to the technical field of the herbicides,especially that of the herbicides for selective control of weeds andweed grasses in crops of useful plants.

WO 2011/035874 A1 describes N-(1,2,5-oxadiazol-3-yl)arylcarboxamides asherbicides. WO 2012/028579 A1 discloses herbicidally activeN-(tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxamides. WO 2012/126932A1 describes N-(1,3,4-oxadiazol-2-yl)arylcarboxamides as herbicides.

AL Y, A. S. ET AL: “Synthesis and reactions of some derivatives of2-amino-5-(4-pyridyl)-1,3,4-oxadiazole”, EGYPTIAN JOURNAL OFPHARMACEUTICAL SCIENCES, 33(3-4), 699-711, 1992, discloses the compoundN-benzoyl-N-[5-(pyridin-4-yl)-1,3,4-oxadiazol-2-yl]benzamide.

SHCHIPANOV, V. P.: “Tautomerism of 5-aminotetrazole. VII. Synthesis,structure, and spectra of diacyl derivatives of 1- and2-methyl-5-aminotetrazoles”, KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII,(5), 923-926, 1969, discloses the compoundsN-acetyl-N-(1-methyltetrazol-5-yl)benzamide andN-benzoyl-N-(1-methyltetrazol-5-yl)benzamide.

GEHLEN, HEINZ ET AL: “2-Amino-1,3,4-oxadiazoles. VIII. Formation of2-amino-5-aminoalkyl-1,3,4-oxadiazoles and their conversion into1,2,4-triazoles and triazolones”, JUSTUS LIEBIGS ANNALEN DER CHEMIE,651, 128-132, 1962, discloses the compoundN-benzoyl-N-{5-[4-({[-(methylsulfonyl)phenyl]amino}methyl)phenyl]-1,3,4-oxadiazol-2-yl}benzamide.

There is no description of any herbicidal effect of the compoundsdisclosed in the three aforementioned documents.

It was an object of the present invention to provide furtherherbicidally active compounds.

It has now been found that benzoylamides substituted by particularradicals on the nitrogen atom are of particularly good suitability asherbicides.

The present invention thus provides N-(1,2,5-oxadiazol-3-yl)-,N-(1,3,4-oxadiazol-2-yl)-, N-(tetrazol-5-yl)- andN-(triazol-5-yl)arylcarboxamides or salts thereof of the formula (I)

in which the symbols and indices are defined as follows:

R is hydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-haloalkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,(C₃-C₆)-halocycloalkyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkyl-S(O)_(n)R²,(C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-OSO₂R²,(C₁-C₆)-alkyl-COOR¹, (C₁-C₆)-alkyl-C(O)R¹, (C₁-C₆)-alkyl-CN,(C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂,(C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R², COOR¹, CON(R¹)₂, orphenyl, heteroaryl, heterocyclyl or benzyl, each substituted by sradicals from the group consisting of X, Y, Z and V,

W is N or CY,

X and Z are each independently hydrogen, nitro, halogen, cyano, formyl,thiocyanato, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-haloalkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-halocycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, (C₃-C₆)-halocycloalkyl-(C₁-C₆)-alkyl,COR′, OR′, OCOR¹, OSO₂R², S(O)_(n)R², SO₂OR¹, SO₂N(R¹)₂, NR¹SO₂R²,NR¹COR¹, (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹,(C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-COOR¹,(C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂,(C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R², NR₁R₂, P(O)(OR⁵)₂, orheteroaryl, heterocyclyl or phenyl, each substituted by s radicals fromthe group of methyl, ethyl, methoxy, nitro, trifluoromethyl and halogen,

Y is hydrogen, nitro, halogen, cyano, thiocyanato, (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkenyl, halo-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,COW, COOR¹, OCOOR¹, NR¹COOR¹, C(O)N(R¹)₂, NR¹C(O)N(R¹)₂, OC(O)N(R¹)₂,C(O)N(R¹)OR¹, NR¹SO₂R², NR¹COR¹, OR¹, OSO₂R², S(O)_(n)R², SO₂OR¹,SO₂N(R¹)₂ (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹,(C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-CO₂R¹,(C₁-C₆)-alkyl-CN, (C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂,(C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R²,N(R¹)₂, P(O)(OR⁵)₂, CH₂P(O)(OR⁵)₂, CH═NOR¹, (C₁-C₆)-alkyl-CH═NOR¹,(C₁-C₆)-alkyl-O—N═C(R¹)₂, (C₁-C₆)-alkylphenyl, (C₁-C₆)-alkylheteroaryl,(C₁-C₆)-alkylheterocyclyl, phenyl, heteroaryl or heterocyclyl, where the6 latter radicals are each substituted by s radicals from the groupconsisting of halogen, nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy,halo-(C₁-C₆)-alkoxy, (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl and cyanomethyl, andwhere heterocyclyl bears n oxo groups, or

Y and Z together with the two atoms to which they are bonded form a 5-,6- or 7-membered, unsaturated, partly saturated or saturated ring which,as well as carbon atoms, in each case comprises s nitrogen atoms, noxygen atoms, n sulfur atoms and n S(O), S(O)₂, C═N—R¹⁷, C(OR¹⁷)₂,C[—O—(CH₂)₂—O—] or C(O) elements as ring members, wherein the carbonatoms are substituted by s radicals from the group consisting ofhalogen, cyano, (C₁-C₆)-alkyl, (C₂-C₁₀)-alkenyl, (C₂-C₁₀)-alkynyl,(C₁-C₆)-haloalkyl, (C₁-C₆)-alkoxy, phenoxy, halo-(C₁-C₆)-alkoxy,(C₃-C₈)-cycloalkyl, (C₂-C₈)-alkoxyalkyl and phenyl,

wherein the nitrogen atoms are substituted by n radicals from the groupconsisting of (C₁-C₆)-alkyl and phenyl,

and in which the aforementioned phenyl radicals are substituted by sradicals from the group consisting of cyano, nitro, halogen,(C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl and (C₁-C₆)-alkoxy,

V is hydrogen, nitro, halogen, cyano, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,OR¹, S(O)_(n)R²,

R¹ is hydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, (C₃-C₆)-halocycloalkyl,(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl,phenyl-(C₁-C₆)-alkyl, heteroaryl, (C₁-C₆)-alkylheteroaryl, heterocyclyl,(C₁-C₆)-alkylheterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,(C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR³-heteroaryl or(C₁-C₆)-alkyl-NR³-heterocyclyl, where the 21 latter radicals aresubstituted by s radicals from the group consisting of cyano, halogen,nitro, thiocyanato, OR³, S(O)_(n)R⁴, N(R³)₂, NR³OR³, COR³, OCOR³, SCOR⁴,NR³COR³, NR³SO₂R⁴, CO₂R³, COSR⁴, CON(R³)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl bears noxo groups,

R² is (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, (C₃-C₆)-halocycloalkyl,(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl,phenyl-(C₁-C₆)-alkyl, heteroaryl, (C₁-C₆)-alkylheteroaryl, heterocyclyl,(C₁-C₆)-alkylheterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,(C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR³-heteroaryl,(C₁-C₆)-alkyl-NR³-heterocyclyl, where the 21 latter radicals aresubstituted by s radicals from the group consisting of cyano, halogen,nitro, thiocyanato, OR³, S(O)_(n)R⁴, N(R³)₂, NR³OR³, COR³, OCOR³, SCOR⁴,NR³COR³, NR³SO₂R⁴, CO₂R³, COSR⁴, CON(R³)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl bears noxo groups,

R³ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl or (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,

R⁴ is (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl or (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,

R⁵ is (C₁-C₄)-alkyl,

-   -   n is 0, 1 or 2,    -   s is 0, 1, 2 or 3,    -   Q is a Q1, Q2, Q3 or Q4 radical

R⁶ and R⁷ are independently (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl,

where these 6 aforementioned radicals are each substituted by s radicalsfrom the group consisting of nitro, cyano, SiR¹² ₃, PO(OR¹²)₃,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy, N(R¹⁰)₂,COR¹⁰, COOR¹⁰, OCOR¹⁰, OCO₂R¹⁰, NR¹⁰COR¹⁰, NR¹⁰SO₂R¹¹,(C₃-C₆)-cycloalkyl, heteroaryl, heterocyclyl, phenyl, D-heteroaryl,D-heterocyclyl, D-phenyl or D-benzyl, and where the 7 latter radicalsare substituted by s radicals from the group of methyl, ethyl, methoxy,trifluoromethyl and halogen, and where heterocyclyl bears n oxo groups,or

R⁶ and R⁷ are each (C₃-C₇)-cycloalkyl, heteroaryl, heterocyclyl orphenyl, each substituted by s radicals from the group consisting ofhalogen, nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy,halo-(C₁-C₆)-alkoxy and (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl,

R⁸ is hydrogen, (C₁-C₆)-alkyl, (C₃-C₇)-cycloalkyl, halo-(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy, (C₂-C₆)-alkenyl,(C₂-C₆)-alkenyloxy, halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₂-C₆)-alkynyloxy, halo-(C₂-C₆)-alkynyl, cyano, nitro, methylsulfenyl,methylsulfinyl, methylsulfonyl, (C₁-C₆)-alkylcarbonylamino,(C₁-C₆)-alkoxycarbonylamino, benzoylamino, methoxycarbonyl,ethoxycarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, benzoyl,methylcarbonyl, piperidinylcarbonyl, trifluoromethylcarbonyl, halogen,amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl,methoxymethyl, or heteroaryl, heterocyclyl or phenyl, each substitutedby s radicals from the group consisting of methyl, ethyl, methoxy,trifluoromethyl and halogen;

R⁹ is hydrogen, (C₁-C₆)-alkyl, R¹³O—(C₁-C₆)-alkyl, CH₂R¹⁴,(C₃-C₇)-cycloalkyl, halo-(C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl, OR¹³, NHR¹³, methoxycarbonyl,ethoxycarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl,methylcarbonyl, trifluoromethylcarbonyl, dimethylamino, acetylamino,methylsulfenyl, methylsulfinyl, methylsulfonyl, or heteroaryl,heterocyclyl, benzyl or phenyl, each substituted by s radicals from thegroup consisting of halogen, nitro, cyano, (C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy,halo-(C₁-C₆)-alkoxy and (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl,

R¹⁰ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl or (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl or phenyl,

R¹¹ is (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl or phenyl,

R¹² is (C₁-C)-alkyl,

R¹³ is hydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, (C₃-C₆)-halocycloalkyl,(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl,phenyl-(C₁-C₆)-alkyl, heteroaryl, (C₁-C₆)-alkylheteroaryl, heterocyclyl,(C₁-C₆)-alkylheterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,(C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR¹⁵-heteroaryl or(C₁-C₆)-alkyl-NR¹⁵-heterocyclyl, where the 21 latter radicals aresubstituted by s radicals from the group consisting of cyano, halogen,nitro, thiocyanato, OR¹⁵, S(O)_(n)R¹⁶, N(R¹⁵)₂, NR¹⁵OR¹⁵, COR¹⁵, OCOR¹⁵,SCOR¹⁶, NR¹⁵COR¹⁵, NR¹⁵SO₂R¹⁶, CO₂R¹⁵, COSR¹⁶, CON(R¹⁵)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl bears noxo groups,

R¹⁴ is acetoxy, acetamido, N-methylacetamido, benzoyloxy, benzamido,N-methylbenzamido, methoxycarbonyl, ethoxycarbonyl, benzoyl,methylcarbonyl, piperidinylcarbonyl, morpholinylcarbonyl,trifluoromethylcarbonyl, aminocarbonyl, methylaminocarbonyl,dimethylaminocarbonyl, (C₃-C₆)-alkoxy, (C₃-C₆)-cycloalkyl, orheteroaryl, heterocyclyl or phenyl, each substituted by s radicals fromthe group consisting of methyl, ethyl, methoxy, trifluoromethyl andhalogen;

R¹⁵ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl or (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,

R¹⁶ is (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl,

R¹⁷ is (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy andhalo-(C₁-C₆)-alkoxy,

s is 0, 1, 2 or 3,

n is 0, 1 or 2,

D is O, S, or NR¹¹,

with the proviso that V, W, X, Y and Z are not simultaneously hydrogen.

Preference is given to compounds of the general formula (I) in which

R is hydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-haloalkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,(C₃-C₆)-halocycloalkyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkyl-S(O)_(n)R²,(C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-OSO₂R²,(C₁-C₆)-alkyl-COOR¹, (C₁-C₆)-alkyl-C(O)R¹, (C₁-C₆)-alkyl-CN,(C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂,(C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R², COOR¹, CON(R¹)₂, orphenyl, heteroaryl, heterocyclyl or benzyl, each substituted by sradicals from the group consisting of X, Y, Z and V,

W is N or CY,

X and Z are each independently hydrogen, halogen, (C₁-C₆)-alkyl,(C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl, (C₃-C₆)-cycloalkyl,(C₃-C₆)-halocycloalkyl, OR¹, S(O)_(n)R², SO₂N(R¹)₂, NR¹SO₂R², NR¹COR¹,(C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, or heteroaryl, heterocyclylor phenyl, each substituted by s radicals from the group of methyl,ethyl, methoxy, nitro, trifluoromethyl and halogen,

Y is hydrogen, (C₂-C₆)-alkenyl, COR¹, CO₂R¹, OCO₂R¹, NR¹CO₂R¹,C(O)N(R¹)₂, NR¹C(O)N(R¹)₂, OC(O)N(R¹)₂, C(O)N(R¹)OR¹, NR¹SO₂R², NR¹COR¹,OR¹, S(O)_(n)R², SO₂N(R¹)₂, (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹,(C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-CO₂R¹, (C₁-C₆)-alkyl-CON(R¹)₂,(C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R²,N(R¹)₂, CH═NOR¹, (C₁-C₆)-alkyl-CH═NOR¹, (C₁-C₆)-alkylheteroaryl,(C₁-C₆)-alkylheterocyclyl, heteroaryl or heterocyclyl, where the 4latter radicals are each substituted by s radicals from the groupconsisting of halogen, nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy,halo-(C₁-C₆)-alkoxy, (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl and cyanomethyl, andwhere heterocyclyl bears n oxo groups,

V is hydrogen, Cl, OMe, methyl or ethyl,

R¹ is hydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, (C₃-C₆)-halocycloalkyl,(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl,phenyl-(C₁-C₆)-alkyl, heteroaryl, (C₁-C₆)-alkylheteroaryl, heterocyclyl,(C₁-C₆)-alkylheterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,(C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR³-heteroaryl or(C₁-C₆)-alkyl-NR³-heterocyclyl, where the 21 latter radicals aresubstituted by s radicals from the group consisting of cyano, halogen,nitro, thiocyanato, OR³, S(O)_(n)R⁴, N(R³)₂, NR³OR³, COR³, OCOR³, SCOR⁴,NR³COR³, NR³SO₂R⁴, CO₂R³, COSR⁴, CON(R³)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl bears noxo groups,

R² is (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, (C₃-C₆)-halocycloalkyl,(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl,phenyl-(C₁-C₆)-alkyl, heteroaryl, (C₁-C₆)-alkylheteroaryl, heterocyclyl,(C₁-C₆)-alkylheterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,(C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR³-heteroaryl,(C₁-C₆)-alkyl-NR³-heterocyclyl, where the 21 latter radicals aresubstituted by s radicals from the group consisting of cyano, halogen,nitro, thiocyanato, OR³, S(O)_(n)R⁴, N(R³)₂, NR³OR³, COR³, OCOR³, SCOR⁴,NR³COR³, NR³SO₂R⁴, CO₂R³, COSR⁴, CON(R³)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl bears noxo groups,

R³ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl or (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,

R⁴ is (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl or (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,

n is 0, 1 or 2,

s is 0, 1, 2 or 3,

Q is a Q1, Q2, Q3 or Q4 radical

R⁶ and R⁷ are independently (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₂-C₆)-alkenyl, where these 3 aforementioned radicals are eachsubstituted by s (C₁-C₆)-alkoxy radicals,

R⁸ is chlorine, methyl, methoxymethyl, amino or acetylamino,

R⁹ is methyl, ethyl, methoxymethyl or methoxyethyl, with the provisothat V, W, X, Y and Z are not simultaneously hydrogen.

Particular preference is given to compounds of the general formula (I)in which R is methyl, or phenyl substituted in each case by s radicalsfrom the group consisting of X, Y and Z,

W is CY,

X is F, C₁, Br, methyl, ethyl, cyclopropyl, trifluoromethyl, methoxy,methoxymethyl, methoxyethoxymethyl, SMe or SO₂Me, Z is hydrogen, F, C₁,Br, I, methyl, ethyl, trifluoromethyl, difluoromethyl, pentafluoroethyl,methylsulfonyl or ethylsulfonyl,

Y is hydrogen, SMe, S(O)Me, SO₂Me, SEt, S(O)Et, SO₂Et, CH₂OMe, CH₂OEt,CH₂OCH₂CF₃, CH₂SMe, CH₂S(O)Me, CH₂SO₂Me, vinyl, C(O)Me, C(O)Et, C(O)cPr,CO₂Me, CHN═OMe, 4,5-dihydro-1,2-oxazol-3-yl,5-methyl-4,5-dihydro-1,2-oxazol-3-yl,5-methyl-4,5-dihydro-1,2-oxazol-3-yl,5-cyanomethyl-4,5-dihydro-1,2-oxazol-3-yl, 4,5-dihydro-1,2-oxazol-5-yl,3-methyl-4,5-dihydro-1,2-oxazol-5-yl, 1H-pyrazol-1-yl,1H-1,2,3-triazol-1-yl, 2H-1,2,3-triazol-2-yl, 1H-1,2,4-triazol-1-yl,pyrolidin-2-on-1-yl, morpholin-3-on-4-yl, OMe, OEt, OnPr, OCH₂cPr,OCH₂CH₂F; OCH₂CH₂OMe or OCH₂CH₂CH₂OMe,

V is hydrogen,

Q is a Q1, Q2, Q3 or Q4 radical

R⁶ is methyl or ethyl,

R⁷ is methyl,

R⁸ is chlorine or methyl,

R⁹ is methyl,

s is 0, 1, 2 or 3.

In the formula (I) and all the formulae which follow, alkyl radicalshaving more than two carbon atoms may be straight-chain or branched.Alkyl radicals are, for example, methyl, ethyl, n-propyl or isopropyl,n-, iso-, t- or 2-butyl, pentyls, hexyls such as n-hexyl, isohexyl and1,3-dimethylbutyl. Analogously, alkenyl is, for example, allyl,1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl,but-3-en-1-yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl. Alkynylis, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl,1-methylbut-3-yn-1-yl. The multiple bond may be in any position in eachunsaturated radical. Cycloalkyl is a carbocyclic saturated ring systemhaving three to six carbon atoms, for example cyclopropyl, cyclobutyl,cyclopentyl or cyclohexyl. Analogously, cycloalkenyl is a monocyclicalkenyl group having three to six carbon ring members, for examplecyclopropenyl, cyclobutenyl, cyclopentenyl and cyclohexenyl, where thedouble bond may be in any position.

Halogen is fluorine, chlorine, bromine or iodine.

Heterocyclyl is a saturated, partly saturated or fully unsaturatedcyclic radical which contains 3 to 6 ring atoms, of which 1 to 4 arefrom the group of oxygen, nitrogen and sulfur, and which mayadditionally be fused by a benzo ring. For example, heterocyclyl ispiperidinyl, pyrrolidinyl, tetrahydrofuranyl, dihydrofuranyl andoxetanyl.

Heteroaryl is an aromatic cyclic radical which contains 3 to 6 ringatoms, of which 1 to 4 are from the group of oxygen, nitrogen andsulfur, and which may additionally be fused by a benzo ring. Forexample, heteroaryl is benzimidazol-2-yl, furanyl, imidazolyl,isoxazolyl, isothiazolyl, oxazolyl, pyrazinyl, pyrimidinyl, pyridazinyl,pyridinyl, benzisoxazolyl, thiazolyl, pyrrolyl, pyrazolyl, thiophenyl,1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl,1,3,4-oxadiazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,2,5-triazolyl,1,3,4-triazolyl, 1,2,4-triazolyl, 1,2,4-thiadiazolyl,1,3,4-thiadiazolyl, 1,2,3-thiadiazolyl, 1,2,5-thiadiazolyl,2H-1,2,3,4-tetrazolyl, 1H-1,2,3,4-tetrazolyl, 1,2,3,4-oxatriazolyl,1,2,3,5-oxatriazolyl, 1,2,3,4-thiatriazolyland 1,2,3,5-thiatriazolyl.

If a group is polysubstituted by radicals, this should be understood tomean that this group is substituted by one or more identical ordifferent radicals selected from the radicals mentioned. The sameapplies to the formation of ring systems by different atoms andelements. At the same time, the scope of the claims shall exclude thosecompounds known by the person skilled in the art to be chemicallyunstable under standard conditions.

Depending on the nature of the substituents and the manner in which theyare attached, the compounds of the general formula (I) may be present asstereoisomers. If, for example, one or more asymmetric carbon atoms arepresent, enantiomers and diastereomers may occur. Stereoisomers likewiseoccur when n is 1 (sulfoxides). Stereoisomers can be obtained from themixtures obtained in the preparation by customary separation methods,for example by chromatographic separation processes. It is likewisepossible to selectively prepare stereoisomers by using stereoselectivereactions with use of optically active starting materials and/orauxiliaries. The invention also relates to all the stereoisomers andmixtures thereof that are encompassed by the general formula (I) but arenot defined specifically. Owing to the oxime ether structure, thecompounds of the invention may also occur as geometric isomers (E/Zisomers). The invention also relates to all the E/Z isomers and mixturesthereof that are encompassed by the general formula (I) but are notdefined specifically.

The compounds of the formula (I) are capable of forming salts. Salts canbe formed by the action of a base on those compounds of the formula (I)which bear an acidic hydrogen atom, for example in the case that R¹contains a COOH group or a sulfonamide group —NHSO₂—. Examples ofsuitable bases are organic amines such as trialkylamines, morpholine,piperidine or pyridine, and the hydroxides, carbonates andhydrogencarbonates of ammonium, alkali metals or alkaline earth metals,especially sodium hydroxide, potassium hydroxide, sodium carbonate,potassium carbonate, sodium hydrogencarbonate and potassiumhydrogencarbonate. These salts are compounds in which the acidichydrogen is replaced by an agriculturally suitable cation, for examplemetal salts, especially alkali metal salts or alkaline earth metalsalts, especially sodium and potassium salts, or else ammonium salts,salts with organic amines or quaternary ammonium salts, for example withcations of the formula [NRR′R″R′″]⁺ in which R to R′″ are eachindependently an organic radical, especially alkyl, aryl, aralkyl oralkylaryl. Also suitable are alkylsulfonium and alkylsulfoxonium salts,such as (C₁-C₄)-trialkylsulfonium and (C₁-C₄)-trialkylsulfoxonium salts.

The compounds of the formula (I) can form salts by addition of asuitable inorganic or organic acid, for example mineral acids, forexample HCl, HBr, H₂SO₄, H₃PO₄ or HNO3, or organic acids, for examplecarboxylic acids such as formic acid, acetic acid, propionic acid,oxalic acid, lactic acid or salicylic acid or sulfonic acids, forexample p-toluenesulfonic acid, onto a basic group, for example amino,alkylamino, dialkylamino, piperidino, morpholino or pyridino. In such acase, these salts will comprise the conjugate base of the acid as theanion.

Inventive compounds can be prepared, for example, by the methodspecified in scheme 1, by reacting arylcarboxamide (II) with an acidchloride or an anhydride of the general formula (III):

The arylcarboxamides of the formula (II) are known in principle and canbe prepared, for example, by the methods described in WO2011/035874 A1,WO2012/123416 A1, WO 2012/028579 A1 and WO2012/126932.

Inventive compounds having two identical acyl radicals can also beprepared, for example, by the method specified in scheme 2, by reactingan amine of the formula (IV) with an acid chloride (V):

Inventive compounds having two identical acyl radicals can also beprepared by the method specified in scheme 3, by reacting an amine ofthe formula (IV) with an acid of the formula (VI):

For the activation, it is possible to use dehydrating reagents which aretypically for amidation reactions, for example 1,1′-carbonyldiimidazole(CDI), dicyclohexylcarbodiimide (DCC),2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (T3P),etc.

The benzoyl chlorides of the formula (V) or their parent benzoic acidsof the formula (VI) are known in principle and can be prepared, forexample, by the methods described in U.S. Pat. No. 6,376,429 B1, EP 1585 742 A1 and EP 1 202 978 A1.

Collections of compounds of the formula (I) which can be synthesized bythe abovementioned reactions can also be prepared in a parallelizedmanner, in which case this may be accomplished in a manual, partlyautomated or fully automated manner. It is possible, for example, toautomate the conduct of the reaction, the workup or the purification ofthe products and/or intermediates. Overall, this is understood to mean aprocedure as described, for example, by D. Tiebes in CombinatorialChemistry Synthesis, Analysis, Screening (editor: Gunther Jung), Wiley,1999, on pages 1 to 34.

For the parallelized conduct of the reaction and workup, it is possibleto use a number of commercially available instruments, for exampleCalypso reaction blocks from Barnstead International, Dubuque, Iowa52004-0797, USA or reaction stations from Radleys, Shirehill, SaffronWalden, Essex, CB11 3AZ, England, or MuItiPROBE Automated Workstationsfrom Perkin Elmer, Waltham, Mass. 02451, USA. For the parallelizedpurification of compounds of the general formula (I) or of intermediateswhich occur in the course of preparation, available apparatuses includechromatography apparatuses, for example from ISCO, Inc., 4700 SuperiorStreet, Lincoln, Nebr. 68504, USA.

The apparatuses detailed lead to a modular procedure in which theindividual working steps are automated, but manual operations have to becarried out between the working steps. This can be circumvented by usingpartly or fully integrated automation systems in which the respectiveautomation modules are operated, for example, by robots. Automationsystems of this type can be obtained, for example, from Caliper,Hopkinton, Mass. 01748, USA.

The implementation of single or multiple synthesis steps can besupported by the use of polymer-supported reagents/scavenger resins. Thespecialist literature describes a series of experimental protocols, forexample in ChemFiles, Vol. 4, No. 1, Polymer-Supported Scavengers andReagents for Solution-Phase Synthesis (Sigma-Aldrich).

Besides the methods described herein, the preparation of compounds ofthe general formula (I) can take place completely or partially bysolid-phase-supported methods. For this purpose, individualintermediates or all intermediates in the synthesis or a synthesisadapted for the corresponding procedure are bound to a synthesis resin.Solid-phase-supported synthesis methods are described adequately in thetechnical literature, for example Barry A. Bunin in “The CombinatorialIndex”, Academic Press, 1998 and Combinatorial Chemistry Synthesis,Analysis, Screening (editor: Gunther Jung), Wiley, 1999. The use ofsolid-phase-supported synthesis methods permits a number of protocols,which are known from the literature and which for their part may beperformed manually or in an automated manner. The reactions can beperformed, for example, by means of IRORI technology in microreactorsfrom Nexus Biosystems, 12140 Community Road, Poway, Calif. 92064, USA.

Both in the solid and in the liquid phase, the implementation ofindividual or several synthesis steps may be supported by the use ofmicrowave technology. The specialist literature describes a series ofexperimental protocols, for example in Microwaves in Organic andMedicinal Chemistry (editor: C. O. Kappe and A. Stadler), Wiley, 2005.

The preparation by the processes described herein gives compounds of theformula (I) in the form of substance collections, which are calledlibraries. The present invention also provides libraries comprising atleast two compounds of the formula (I).

The inventive compounds of the formula (I), referred to hereinbelow as“compounds of the invention”, have an excellent herbicidal effectivenessagainst a broad spectrum of economically important mono- anddicotyledonous annual harmful plants. The active ingredients also havegood control over perennial harmful plants which are difficult tocontrol and produce shoots from rhizomes, root stocks or other perennialorgans.

The present invention therefore also provides a method for controllingunwanted plants or for regulating the growth of plants, preferably inplant crops, in which one or more compound(s) of the invention is/areapplied to the plants (for example harmful plants such asmonocotyledonous or dicotyledonous weeds or unwanted crop plants), theseed (for example grains, seeds or vegetative propagules such as tubersor shoot parts with buds) or the area on which the plants grow (forexample the area under cultivation). The compounds of the invention canbe deployed, for example, prior to sowing (if appropriate also byincorporation into the soil), prior to emergence or after emergence.Specific examples of some representatives of the monocotyledonous anddicotyledonous weed flora which can be controlled by the compounds ofthe invention are as follows, though the enumeration is not intended toimpose a restriction to particular species.

Monocotyledonous harmful plants of the genera: Aegilops, Agropyron,Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus,Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa,Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis,Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria,Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria,Scirpus, Setaria, Sorghum.

Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia,Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella,Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura,Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium,Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria,Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago,Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex,Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola,Xanthium.

If the compounds of the invention are applied to the soil surface beforegermination, either the emergence of the weed seedlings is preventedcompletely or the weeds grow until they have reached the cotyledonstage, but then they stop growing and ultimately die completely afterthree to four weeks have passed.

If the active ingredients are applied post-emergence to the green partsof the plants, growth stops after the treatment, and the harmful plantsremain at the growth stage of the point of time of application, or theydie completely after a certain time, so that in this manner competitionby the weeds, which is harmful to the crop plants, is eliminated veryearly and in a sustained manner.

Although the compounds of the invention have outstanding herbicidalactivity against monocotyledonous and dicotyledonous weeds, crop plantsof economically important crops, for example dicotyledonous crops of thegenera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus,Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana,Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous crops of thegenera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum,Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, in particular Zeaand Triticum, will be damaged to a negligible extent only, if at all,depending on the structure of the particular compound of the inventionand its application rate. For these reasons, the present compounds arevery suitable for selective control of unwanted plant growth in plantcrops such as agriculturally useful plants or ornamental plants.

In addition, the compounds of the invention (depending on theirparticular structure and the application rate deployed) have outstandinggrowth-regulating properties in crop plants. They intervene in theplants' own metabolism with regulatory effect, and can thus be used forthe controlled influencing of plant constituents and to facilitateharvesting, for example by triggering desiccation and stunted growth.Furthermore, they are also suitable for the general control andinhibition of unwanted vegetative growth without killing the plants inthe process. Inhibition of vegetative growth plays a major role for manymono- and dicotyledonous crops since, for example, this can reduce orcompletely prevent lodging.

By virtue of their herbicidal and plant growth regulatory properties,the active ingredients can also be used to control harmful plants incrops of genetically modified plants or plants modified by conventionalmutagenesis. In general, the transgenic plants are characterized byparticular advantageous properties, for example by resistances tocertain pesticides, in particular certain herbicides, resistances toplant diseases or pathogens of plant diseases, such as certain insectsor microorganisms such as fungi, bacteria or viruses. Other particularproperties relate, for example, to the harvested material with regard toquantity, quality, storability, composition and specific constituents.For instance, there are known transgenic plants with an elevated starchcontent or altered starch quality, or those with a different fatty acidcomposition in the harvested material.

It is preferable, with respect to transgenic crops, to use the compoundsof the invention in economically important transgenic crops of usefulplants and ornamentals, for example of cereals such as wheat, barley,rye, oats, millet/sorghum, rice and corn or else crops of sugar beet,cotton, soybean, oilseed rape, potato, tomato, peas and other types ofvegetable. Preferably, the compounds of the invention can be used asherbicides in crops of useful plants which are resistant, or have beenmade resistant by genetic engineering, to the phytotoxic effects of theherbicides.

It is preferred to use the compounds of the invention in economicallyimportant transgenic crops of useful plants and ornamentals, for exampleof cereals such as wheat, barley, rye, oats, millet/sorghum, rice,cassava and corn or else crops of sugar beet, cotton, soybean, oilseedrape, potato, tomato, peas and other types other vegetable. Preferably,the compounds of the invention can be used as herbicides in crops ofuseful plants which are resistant, or have been made resistant bygenetic engineering, to the phytotoxic effects of the herbicides.

Conventional ways of producing novel plants which have modifiedproperties in comparison to existing plants consist, for example, intraditional cultivation methods and the generation of mutants.Alternatively, novel plants with modified properties can be generatedwith the aid of recombinant methods (see, for example, EP-A-0221044,EP-A-0131624). For example, there have been descriptions in severalcases of:

-   -   genetic modifications of crop plants for the purpose of        modifying the starch synthesized in the plants (e.g. WO        92/11376, WO 92/14827, WO 91/19806),    -   transgenic crop plants which are resistant to particular        herbicides of the glufosinate type (cf., for example,        EP-A-0242236, EP-A-242246) or glyphosate type (WO 92/00377) or        the sulfonylurea type (EP-A-0257993, U.S. Pat. No. 5,013,659),    -   transgenic crop plants, for example cotton, capable of producing        Bacillus thuringiensis toxins (Bt toxins), which make the plants        resistant to particular pests (EP-A-0142924, EP-A-0193259),    -   transgenic crop plants with a modified fatty acid composition        (WO 91/13972),    -   genetically modified crop plants with novel constituents or        secondary metabolites, for example novel phytoalexins, which        bring about an increased disease resistance (EPA 309862,        EPA0464461),    -   genetically modified plants having reduced photorespiration,        which have higher yields and higher stress tolerance (EPA        0305398),    -   transgenic crop plants which produce pharmaceutically or        diagnostically important proteins (“molecular pharming”),    -   transgenic crop plants which feature higher yields or better        quality,    -   transgenic crop plants which feature, for example, the        abovementioned novel properties (“gene stacking”) through        combinations.

Numerous molecular biology techniques which can be used to produce noveltransgenic plants with modified properties are known in principle; see,for example, I. Potrykus and G. Spangenberg (eds.) Gene Transfer toPlants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg,or Christou, “Trends in Plant Science” 1 (1996) 423-431).

For such recombinant manipulations, nucleic acid molecules which allowmutagenesis or sequence alteration by recombination of DNA sequences canbe introduced into plasmids. With the aid of standard methods, it ispossible, for example, to undertake base exchanges, remove parts ofsequences or add natural or synthetic sequences. To join the DNAfragments with one another, adapters or linkers can be placed onto thefragments, see, for example, Sambrook et al., 1989, Molecular Cloning, ALaboratory Manual, 2nd edition Cold Spring Harbor Laboratory Press, ColdSpring Harbor, N.Y., or Winnacker “Gene and Klone [Genes and clones]”,VCH Weinheim 2nd edition 1996.

For example, the generation of plant cells with a reduced activity of agene product can be achieved by expressing at least one correspondingantisense RNA, a sense RNA for achieving a cosuppression effect, or byexpressing at least one suitably constructed ribozyme which specificallycleaves transcripts of the abovementioned gene product. To this end, itis firstly possible to use DNA molecules which encompass the entirecoding sequence of a gene product inclusive of any flanking sequenceswhich may be present, and also DNA molecules which only encompassportions of the coding sequence, in which case it is necessary for theseportions to be long enough to have an antisense effect in the cells. Itis also possible to use DNA sequences which have a high degree ofhomology to the coding sequences of a gene product, but are notcompletely identical to them.

When expressing nucleic acid molecules in plants, the proteinsynthesized may be localized in any desired compartment of the plantcell. However, to achieve localization in a particular compartment, itis possible, for example, to join the coding region to DNA sequenceswhich ensure localization in a particular compartment. Such sequencesare known to those skilled in the art (see, for example, Braun et al.,EMBO J. 11 (1992), 3219-3227, Wolter et al., Proc. Natl. Acad. Sci. USA85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106). Thenucleic acid molecules can also be expressed in the organelles of theplant cells.

The transgenic plant cells can be regenerated by known techniques togive rise to entire plants. In principle, the transgenic plants may beplants of any desired plant species, i.e. not only monocotyledonous butalso dicotyledonous plants.

Thus, transgenic plants can be obtained whose properties are altered byoverexpression, suppression or inhibition of homologous (=natural) genesor gene sequences or expression of heterologous (=foreign) genes or genesequences.

The compounds of the invention can be used with preference in transgeniccrops which are resistant to growth regulators, for example dicamba, orto herbicides which inhibit essential plant enzymes, for exampleacetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS)or hydroxyphenylpyruvate dioxygenases (HPPD), or to herbicides from thegroup of the sulfonylureas, the glyphosates, glufosinates orbenzoylisoxazoles and analogous active ingredients.

When the active ingredients of the invention are employed in transgeniccrops, not only do the effects toward harmful plants observed in othercrops occur, but frequently also effects which are specific toapplication in the particular transgenic crop, for example an altered orspecifically widened spectrum of weeds which can be controlled, alteredapplication rates which can be used for the application, preferably goodcombinability with the herbicides to which the transgenic crop isresistant, and influencing of growth and yield of the transgenic cropplants.

The invention therefore also provides for the use of the compounds ofthe invention as herbicides for control of harmful plants in transgeniccrop plants.

The compounds of the invention can be applied in the form of wettablepowders, emulsifiable concentrates, sprayable solutions, dustingproducts or granules in the customary formulations. The inventiontherefore also provides herbicidal and plant-growth-regulatingcompositions which comprise the compounds of the invention.

The compounds of the invention can be formulated in various ways,according to the biological and/or physicochemical parameters required.Possible formulations include, for example: wettable powders (WP),water-soluble powders (SP), water-soluble concentrates, emulsifiableconcentrates (EC), emulsions (EW), such as oil-in-water and water-in-oilemulsions, sprayable solutions, suspension concentrates (SC),dispersions based on oil or water, oil-miscible solutions, capsulesuspensions (CS), dusting products (DP), dressings, granules forscattering and soil application, granules (GR) in the form ofmicrogranules, spray granules, absorption and adsorption granules,water-dispersible granules (WG), water-soluble granules (SG), ULVformulations, microcapsules and waxes.

These individual formulation types are known in principle and aredescribed, for example, in: Winnacker-Kuchler, “Chemische Technologie”[Chemical Technology], volume 7, C. Hanser Verlag Munich, 4th Ed. 1986,Wade van Valkenburg, “Pesticide Formulations”, Marcel Dekker, N.Y.,1973, K. Martens, “Spray Drying” Handbook, 3rd Ed. 1979, G. Goodwin Ltd.London.

The formulation auxiliaries required, such as inert materials,surfactants, solvents and further additives, are likewise known and aredescribed, for example, in: Watkins, “Handbook of Insecticide DustDiluents and Carriers”, 2nd Ed., Darland Books, Caldwell N.J.; H. v.Olphen, “Introduction to Clay Colloid Chemistry”, 2nd Ed., J. Wiley &Sons, N.Y.; C. Marsden, “Solvents Guide”, 2nd Ed., Interscience, N.Y.1963; McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ. Corp.,Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface ActiveAgents”, Chem. Publ. Co. Inc., N.Y. 1964; SchOnfeldt,“Grenzflachenaktive Athylenoxidaddukte” [Interface-active Ethylene OxideAdducts], Wiss. Verlagsgesellschaft, Stuttgart 1976; Winnacker-Kuchler,“Chemische Technologie” [Chemical Engineering], volume 7, C. HanserVerlag Munich, 4th Ed. 1986.

On the basis of these formulations, it is also possible to producecombinations with other pesticidally active substances, for exampleinsecticides, acaricides, herbicides, fungicides, and also withsafeners, fertilizers and/or growth regulators, for example in the formof a finished formulation or as a tankmix. Suitable safeners are, forexample, mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl,cloquintocet-mexyl and dichlormid.

Wettable powders are preparations which can be dispersed uniformly inwater and, in addition to the active ingredient, apart from a diluent orinert substance, also comprise surfactants of the ionic and/or nonionictype (wetting agents, dispersants), for example polyoxyethylatedalkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fattyamines, fatty alcohol polyglycol ether sulfates, alkanesulfonates,alkylbenzenesulfonates, sodium lignosulfonate, sodium2,2′-dinaphthylmethane-6,6′-disulfonate, sodiumdibutylnaphthalenesulfonate or else sodium oleoylmethyltaurate. Toproduce the wettable powders, the active herbicidal ingredients arefinely ground, for example in customary apparatuses such as hammermills, blower mills and air-jet mills, and simultaneously orsubsequently mixed with the formulation auxiliaries.

Emulsifiable concentrates are produced by dissolving the activeingredient in an organic solvent, for example butanol, cyclohexanone,dimethylformamide, xylene, or else relatively high-boiling aromatics orhydrocarbons or mixtures of the organic solvents, with addition of oneor more ionic and/or nonionic surfactants (emulsifiers).

Examples of emulsifiers which may be used are: calciumalkylarylsulfonates such as calcium dodecylbenzenesulfonate, or nonionicemulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycolethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxidecondensation products, alkyl polyethers, sorbitan esters, for examplesorbitan fatty acid esters, or polyoxyethylene sorbitan esters, forexample polyoxyethylene sorbitan fatty acid esters.

Dusting products are obtained by grinding the active ingredient withfinely distributed solids, for example talc, natural clays, such askaolin, bentonite and pyrophyllite, or diatomaceous earth.

Suspension concentrates may be water- or oil-based. They may beprepared, for example, by wet-grinding by means of commercial bead millsand optional addition of surfactants as have, for example, already beenlisted above for the other formulation types.

Emulsions, for example oil-in-water emulsions (EW), can be produced, forexample, by means of stirrers, colloid mills and/or static mixers usingaqueous organic solvents and optionally surfactants as already listedabove, for example, for the other formulation types.

Granules can be produced either by spraying the active ingredient ontoadsorptive granular inert material or by applying active ingredientconcentrates to the surface of carriers, such as sand, kaolinites orgranular inert material, by means of adhesives, for example polyvinylalcohol, sodium polyacrylate or else mineral oils. Suitable activeingredients can also be granulated in the manner customary for theproduction of fertilizer granules—if desired as a mixture withfertilizers.

Water-dispersible granules are produced generally by the customaryprocesses such as spray-drying, fluidized-bed granulation, pangranulation, mixing with high-speed mixers and extrusion without solidinert material.

For the production of pan, fluidized-bed, extruder and spray granules,see e.g. processes in “Spray-Drying Handbook” 3rd Ed. 1979, G. GoodwinLtd., London, J. E. Browning, “Agglomeration”, Chemical and Engineering1967, pages 147 ff.; “Perry's Chemical Engineer's Handbook”, 5th Ed.,McGraw-Hill, New York 1973, pp. 8-57.

For further details regarding the formulation of crop protectioncompositions, see, for example, G. C. Klingman, “Weed Control as aScience”, John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J.D. Freyer, S. A. Evans, “Weed Control Handbook”, 5th Ed., BlackwellScientific Publications, Oxford, 1968, pages 101-103.

The agrochemical preparations contain generally 0.1 to 99% by weight,especially 0.1 to 95% by weight, of compounds of the invention.

In wettable powders, the active ingredient concentration is, forexample, about 10 to 90% by weight, the remainder to 100% by weightconsisting of customary formulation constituents. In emulsifiableconcentrates, the active ingredient concentration may be about 1% to 90%and preferably 5% to 80% by weight. Dust-type formulations contain 1% to30% by weight of active ingredient, preferably usually 5% to 20% byweight of active ingredient; sprayable solutions contain about 0.05% to80% by weight, preferably 2% to 50% by weight of active ingredient. Inthe case of water-dispersible granules, the active ingredient contentdepends partially on whether the active compound is in liquid or solidform and on which granulation auxiliaries, fillers, etc., are used. Inthe water-dispersible granules, the content of active ingredient is, forexample, between 1% and 95% by weight, preferably between 10% and 80% byweight.

In addition, the active ingredient formulations mentioned optionallycomprise the respective customary stickers, wetters, dispersants,emulsifiers, penetrants, preservatives, antifreeze agents and solvents,fillers, carriers and dyes, defoamers, evaporation inhibitors and agentswhich influence the pH and the viscosity.

For application, the formulations in commercial form are, ifappropriate, diluted in a customary manner, for example in the case ofwettable powders, emulsifiable concentrates, dispersions andwater-dispersible granules with water. Dust-type preparations, granulesfor soil application or granules for scattering and sprayable solutionsare not normally diluted further with other inert substances prior toapplication.

The required application rate of the compounds of the formula (I) varieswith the external conditions, including, inter alia, temperature,humidity and the type of herbicide used. It can vary within wide limits,for example between 0.001 and 1.0 kg/ha or more of active substance, butit is preferably between 0.005 and 750 g/ha.

The examples which follow illustrate the invention.

A. CHEMICAL EXAMPLES 1. Synthesis of2-(methylsulfonyl)-4-trifluoromethyl-N-acetyl-N-(1-methyltetrazol-5-yl)benzamide(Table Example No. 13-1)

To 175 mg (0.5 mmol) of2-(methylsulfonyl)-4-trifluoromethyl-N-(1-methyltetrazol-5-yl)benzamidein 5 ml of THF under argon at 0° C. are added 14 mg (0.55 mmol) ofsodium hydride (95%). After stirring for 10 min, 47 mg (0.6 mmol) ofacetyl chloride are added. The mixture is stirred at 0° C. for 1 h andthen quenched with 2 mL of saturated sodium bicarbonate solution. Themixture is diluted with ethyl acetate and water, and the organic phaseis washed with saturated sodium bicarbonate solution and sodium chloridesolution, dried over Na2SO4 and concentrated. Yield 143 mg (73%).

2. Synthesis of3-(ethoxycarbonyl)-2-methyl-4-(methylsulfanyl)-N-(3-(ethoxycarbonyl)-2-methyl-4-(methylsulfanyl)benzoyl)-N-(1-methyltetrazol-5-yl)benzamide(Table Example No. 1-453)

To 525 mg (2.06 mmol) of3-(ethoxycarbonyl)-2-methyl-4-(methylsulfanyl)benzoic acid, 313 mg (3.09mmol) of 1-methyl-5-aminotetrazole in 3 ml of pyridine are added, whilecooling with an ice bath, 367 mg (3.09 mmol) of thionyl chloride. Themixture is stirred at RT for 3 days, then 0.2 mL of water is added, themixture is stirred at RT for 30 min, and EA and 2 N HCl are added. Theorganic phase removed is washed once again with 2 N HCl and saturatedsodium chloride solution, dried over Na2SO4, concentrated and purifiedby means of RP-HPLC (acetonitrile/water). Yield 112 mg (9%). Anadditional 58 mg (11% yield) of3-(ethoxycarbonyl)-2-methyl-4-(methylsulfanyl)-N-(1-methyltetrazol-5-yl)benzamidewere obtained.

The examples listed in the tables below were prepared analogously to theabovementioned methods or are obtainable analogously to theabovementioned methods. The compounds listed in the tables below arevery particularly preferred.

The abbreviations used mean:

Et=ethyl Me=methyl n-Pr=n-propyl i-Pr=isopropyl c-Pr=cyclopropylPh=phenyl

TABLE 1 Inventive compounds of the formula (I) in which Q is Q1, W isC—Y, R is substituted phenyl and R⁶ is methyl.

Physical data No. X Y Z V (¹H-NMR, DMSO-d₆, 400 MHz) 1-1  F H Cl H 1-2 F H SO₂Me H 1-3  F H SO₂Et H 1-4  F H CF₃ H 1-5  F H NO₂ H 1-6  Cl H BrH 1-7  Cl H SMe H 1-8  Cl H SOMe H 1-9  Cl H SO₂Me H 1-10  Cl H SO₂CH₂ClH 1-11  Cl H SEt H 1-12  Cl H SO₂Et H 1-13  Cl H CF₃ H 1-14  Cl H NO₂ H1-15  Cl H pyrazol-1-yl H 1-16  Cl H 1H-1,2,4- H triazol-1-yl 1-17  Br HCl H 1-18  Br H Br H 1-19  Br H SO₂Me H 1-20  Br H SO₂Et H 1-21  Br HCF₃ H 1-22  SO₂Me H Cl H 1-23  SO₂Me H Br H 1-24  SO₂Me H SMe H 1-25 SO₂Me H SOMe H 1-26  SO₂Me H SO₂Me H 1-27  SO₂Me H SO₂Et H 1-28  SO₂Me HCF₃ H 8.38 (s, 2H), 8.30 (d, 2H), 8.21 (brs, 2H), 4.20 (s, 3H), 3.41 (s,6H), 2.22 (s, 3H) 1-29  SO₂Et H Cl H 1-30  SO₂Et H Br H 1-31  SO₂Et HSMe H 1-32  SO₂Et H SOMe H 1-33  SO₂Et H SO₂Me H 1-34  SO₂Et H CF₃ H1-35  NO₂ H F H 1-36  NO₂ H Cl H 1-37  NO₂ H Br H 1-38  NO₂ H I H 1-39 NO₂ H CN H 1-40  NO₂ H SO₂Me H 1-41  NO₂ H SO₂Et H 1-42  NO₂ H CF₃ H1-43  Me H Cl H 1-44  Me H Br H 1-45  Me H SMe H 1-46  Me H SO₂Me H1-47  Me H SO₂CH₂Cl H 1-48  Me H SEt H 1-49  Me H SO₂Et H 1-50  Me H CF₃H 1-51  CH₂SO₂Me H CF₃ H 1-52  Et H Cl H 1-53  Et H Br H 1-54  Et H SMeH 1-55  Et H SO₂Me H 1-56  Et H SO₂CH₂Cl H 1-57  Et H SEt H 1-58  Et HSO₂Et H 1-59  Et H CF₃ H 1-60  CF₃ H Cl H 1-61  CF₃ H Br H 1-62  CF₃ HSO₂Me H 1-63  CF₃ H SO₂Et H 1-64  CF₃ H CF₃ H 1-65  NO₂ NH₂ F H 1-66 NO₂ NHMe F H 1-67  NO₂ NMe₂ F H 1-68  NO₂ Me Cl H 1-69  NO₂ NH₂ Cl H1-70  NO₂ NHMe Cl H 1-71  NO₂ NMe₂ Cl H 1-72  NO₂ NH₂ Br H 1-73  NO₂NHMe Br H 1-74  NO₂ NMe₂ Br H 1-75  NO₂ NH₂ CF₃ H 1-76  NO₂ NMe₂ CF₃ H1-77  NO₂ NH₂ SO₂Me H 1-78  NO₂ NH₂ SO₂Et H 1-79  NO₂ NHMe SO₂Me H 1-80 NO₂ NMe₂ SO₂Me H 1-81  NO₂ NMe₂ SO₂Et H 1-82  NO₂ NH₂ 1H-1,2,4- Htriazol-1-yl 1-83  NO₂ NHMe 1H-1,2,4- H triazol-1-yl 1-84  NO₂ NMe₂1H-1,2,4- H triazol-1-yl 1-85  Me SMe H H ¹H-NMR (400.1 MHz, CDCl₃):7.518 (0.8); 7.325 (1.0); 7.320 (1.2); 7.310 (0.4); 7.306 (2.3); 7.301(2.3); 7.280 (2.0); 7.272 (0.3); 7.2694 (0.4); 7.2687 (0.4); 7.268(0.5); 7.266 (0.7); 7.265 (0.9); 7.259 (133.8); 7.242 (1.8); 7.170(1.5); 7.166 (1.6); 7.150 (1.1); 7.146 (1.1); 6.995 (0.7); 5.298 (1.0);4.107 (9.8); 2.446 (16.0); 1.527 (33.0); 0.008 (1.6) 1-86  Me SOMe H H8.10-8.06 (m, 2H), 7.69-7.60 (m, 4H), 4.10 (s, 3H), 2.79 (s, 6H), 1-87 Me SO₂Me H H 1-88  Me SEt H H 1-89  Me SOEt H H 1-90  Me SO₂Et H H 1-91 Me S(CH₂)₂OMe H H 1-92  Me SO(CH₂)₂OMe H H 1-93  Me SO₂(CH₂)₂OMe H H1-94  Me F F H 1-95  Me F SMe H 1-96  Me SEt F H 1-97  Me SOEt F H 1-98 Me SO₂Et F H 1-99  Me Me Cl H 1-100 Me F Cl H 1-101 Me Cl Cl H 1-102 MeNH₂ Cl H 1-103 Me NHMe Cl H 1-104 Me NMe₂ Cl H 1-105 Me O(CH₂)₂OMe Cl H1-106 Me O(CH₂)₃OMe Cl H 1-107 Me O(CH₂)₄OMe Cl H 1-108 Me OCH₂CONMe₂ ClH 1-109 Me O(CH₂)₂—CO—NMe₂ Cl H 1-110 Me O(CH₂)₂—NH(CO)NMe₂ Cl H 1-111Me O(CH₂)₂—NH(CO)NHCO₂Et Cl H 1-112 Me O(CH₂)₂—NHCO₂Me Cl H 1-113 MeOCH₂—NHSO₂cPr Cl H 1-114 Me O(CH₂)-5-2,4- Cl H dimethyl-2,4-dihydro-3H-1,2,4- triazol-3-one 1-115 Me O(CH₂)-3,5- Cl Hdimethyl-1,2-oxazol- 4-yl 1-116 Me SMe Cl H 1-117 Me SOMe Cl H 1-118 MeSO₂Me Cl H 1-119 Me SEt Cl H 1-120 Me SOEt Cl H 1-121 Me SO₂Et Cl H1-122 Me S(CH₂)₂OMe Cl H 1-123 Me SO(CH₂)₂OMe Cl H 1-124 Me SO₂(CH₂)₂OMeCl H 1-125 Me NH₂ Br H 1-126 Me NHMe Br H 1-127 Me NMe₂ Br H 1-128 MeOCH₂(CO)NMe₂ Br H 1-129 Me O(CH₂)-5-pyrrolidin- Br H 2-one 1-130 Me SMeBr H 1-131 Me SOMe Br H 1-132 Me SO₂Me Br H 1-133 Me SEt Br H 1-134 MeSOEt Br H 1-135 Me SO₂Et Br H 1-136 Me SMe I H 1-137 Me SOMe I H 1-138Me SO₂Me I H 1-139 Me SEt I H 1-140 Me SOEt I H 1-141 Me SO₂Et I H 1-142Me Cl CF₃ H 1-143 Me SMe CF₃ H 1-144 Me SOMe CF₃ H 1-145 Me SO₂Me CF₃ H1-146 Me SEt CF₃ H 1-147 Me SOEt CF₃ H 1-148 Me SO₂Et CF₃ H 1-149 MeS(CH₂)₂OMe CF₃ H 1-150 Me SO₂(CH₂)₂OMe CF₃ H 1-151 Me SO₂(CH₂)₂OMe CF₃ H1-152 Me Me SO₂Me H 1-153 Me 4,5-dihydro-1,2- SO₂Me H oxazol-3-yl 1-154Me 4,5-dihydro-1,2- SO₂Et H oxazol-3-yl 1-155 Me 5-cyanomethyl-4,5-SO₂Me H dihydro-1,2-oxazol- 3-yl 1-156 Me 5-cyanomethyl-4,5- SO₂Et Hdihydro-1,2-oxazol- 3-yl 1-157 Me NH₂ SO₂Me H 1-158 Me NHMe SO₂Me H1-159 Me NMe₂ SO₂Me H 1-160 Me NH(CH₂)₂OMe SO₂Me H 1-161 Me pyrazol-1-ylSO₂Me H 1-162 Me OH SO₂Me H 1-163 Me OMe SO₂Me H 1-164 Me OMe SO₂Et H1-165 Me OEt SO₂Me H 1-166 Me OEt SO₂Et H 1-167 Me O-i-Pr SO₂Me H 1-168Me O-i-Pr SO₂Et H 1-169 Me O(CH₂)₂OMe SO₂Me H 1-170 Me O(CH₂)₂OMe SO₂EtH 1-171 Me O(CH₂)₃OMe SO₂Me H 1-172 Me O(CH₂)₃OMe SO₂Et H 1-173 MeO(CH₂)₄OMe SO₂Me H 1-174 Me O(CH₂)₄OMe SO₂Et H 1-175 Me O(CH₂)₂NHSO2MeSO₂Me H 1-176 Me O(CH₂)₂NHSO2Me SO₂Et H 1-177 Me OCH₂(CO)NMe₂ SO₂Me H1-178 Me OCH₂(CO)NMe₂ SO₂Et H 1-179 Me [1,4]dioxan-2- SO₂Me H ylmethoxy1-180 Me [1,4]dioxan-2- SO₂Et H ylmethoxy 1-181 Me O(CH₂)₂—O-(3,5-diSO₂Me H methoxypyrimidin-2- yl) 1-182 Me Cl SO₂Me H 1-183 Me SMe SO₂Me H1-184 Me SOMe SO₂Me H 1-185 Me SO₂Me SO₂Me H 1-186 Me SO₂Me SO₂Et H1-187 Me SEt SO₂Me H 1-188 Me SOEt SO₂Me H 1-189 Me SO₂Et SO₂Me H 1-190Me S(CH₂)₂OMe SO₂Me H 1-191 Me SO(CH₂)₂OMe SO₂Me H 1-192 Me SO₂(CH₂)₂OMeSO2Me H 1-193 CH₂SMe OMe SO₂Me H 1-194 CH₂OMe OMe SO₂Me H 1-195CH₂O(CH₂)₂OMe NH(CH₂)₂OEt SO₂Me H 1-196 CH₂O(CH₂)₂OMe NH(CH₂)₃OEt SO₂MeH 1-197 CH₂O(CH₂)₃OMe OMe SO₂Me H 1-198 CH₂O(CH₂)₂OMe NH(CH₂)₂OMe SO₂MeH 1-199 CH₂O(CH₂)₂OMe NH(CH₂)₃OMe SO₂Me H 1-200 Et SMe Cl H 1-201 EtSO₂Me Cl H 1-202 Et SMe CF₃ H 1-203 Et SO₂Me CF₃ H 1-204 Et F SO₂Me H1-205 Et NH(CH₂)₂OMe SO₂Me H 1-206 i-Pr SO₂Me CF₃ H ¹H-NMR (400.1 MHz,CDCl₃): 7.821 (1.6); 7.801 (1.9); 7.593 (0.8); 7.575 (0.7); 7.263(18.6); 7.260 (18.8); 5.301 (6.9); 5.298 (7.1); 4.312 (0.3); 4.295(0.8); 4.277 (1.1); 4.260 (0.8); 4.242 (0.4); 4.133 (0.4); 4.131 (0.5);4.120 (8.4); 4.117 (8.5); 3.335 (15.8); 3.334 (16.0); 3.266 (1.0); 3.264(1.0); 3.196 (0.8); 3.194 (0.8); 2.046 (1.5); 2.044 (1.5); 1.714 (0.4);1.643 (0.4); 1.640 (0.5); 1.625 (0.4); 1.623 (0.4); 1.521 (12.5); 1.503(12.3); 1.395 (0.5); 1.393 (0.5); 1.378 (0.4); 1.375 (0.4); 1.294 (0.5);1.292 (0.5); 1.279 (0.6); 1.277 (0.9); 1.262 (1.0); 1.259 (1.1); 1.244(0.4); 1.241 (0.5); 0.003 (8.2); 0.000 (8.9) 1-207 cPr SO₂Me CF₃ H 1-208CF₃ O(CH₂)₂OMe F H 1-209 CF₃ O(CH₂)₃OMe F H 1-210 CF₃ OCH₂CONMe₂ F H1-211 CF₃ [1,4]dioxan-2- F H ylmethoxy 1-212 CF₃ O(CH₂)₂OMe Cl H 1-213CF₃ O(CH₂)₃OMe Cl H 1-214 CF₃ OCH₂CONMe₂ Cl H 1-215 CF₃ [1,4]dioxan-2-Cl H ylmethoxy 1-216 CF₃ O(CH₂)₂OMe Br H 1-217 CF₃ O(CH₂)₃OMe Br H 1-218CF₃ OCH₂CONMe₂ Br H 1-219 CF₃ [1,4]dioxan-2- Br H ylmethoxy 1-220 CF₃O(CH₂)₂OMe I H 1-221 CF₃ O(CH₂)₃OMe I H 1-222 CF₃ OCH₂CONMe₂ I H 1-223CF₃ [1,4]dioxan-2- I H ylmethoxy 1-224 CF₃ F SO₂Me H 1-225 CF₃ F SO₂Et H1-226 CF₃ O(CH₂)₂OMe SO₂Me H 1-227 CF₃ O(CH₂)₂OMe SO₂Et H 1-228 CF₃O(CH₂)₃OMe SO₂Me H 1-229 CF₃ O(CH₂)₃OMe SO₂Et H 1-230 CF₃ OCH₂CONMe₂SO₂Me H 1-231 CF₃ OCH₂CONMe₂ SO₂Et H 1-232 CF₃ [1,4]dioxan-2- SO₂Me Hylmethoxy 1-233 CF₃ [1,4]dioxan-2- SO₂Et H ylmethoxy 1-234 F SMe CF₃ H1-235 F SOMe CF₃ H 1-236 Cl Me Cl H 1-237 Cl OCH₂CHCH₂ Cl H 1-238 ClOCH₂CHF₂ Cl H 1-239 Cl O(CH₂)₂OMe Cl H 1-240 Cl OCH₂CONMe₂ Cl H 1-241 ClO(CH₂)-5-pyrrolidin- Cl H 2-one 1-242 Cl SMe Cl H 1-243 Cl SOMe Cl H1-244 Cl SO₂Me Cl H 1-245 Cl F SMe H 1-246 Cl Cl SO₂Me H 1-247 Cl CO₂MeSO₂Me H 1-248 Cl CONMe₂ SO₂Me H 1-249 Cl CONMe(OMe) SO₂Me H 1-250 ClCH₂OMe SO₂Me H 1-251 Cl CH₂OMe SO₂Et H 1-252 Cl CH₂OEt SO₂Me H 1-253 ClCH₂OEt SO₂Et H 1-254 Cl CH₂OCH₂CHF₂ SO₂Me H 1-255 Cl CH₂OCH₂CF₃ SO₂Me H1-256 Cl CH₂OCH₂CF₃ SO₂Et H 1-257 Cl CH₂OCH₂CF₂CHF₂ SO₂Me H 1-258 ClCH₂OcPentyl SO₂Me H 1-259 Cl CH₂PO(OMe)₂ SO₂Me H 1-260 Cl4,5-dihydro-1,2- SMe H oxazol-3-yl 1-261 Cl 4,5-dihydro-1,2- SO₂Me Hoxazol-3-yl 1-262 Cl 4,5-dihydro-1,2- SO₂Et H oxazol-3-yl 1-263 Cl5-cyanomethyl-4,5- SO₂Me H dihydro-1,2-oxazol- 3-yl 1-264 Cl5-cyanomethyl-4,5- SO₂Et H dihydro-1,2-oxazol- 3-yl 1-265 Cl5-(methoxymethyl)- SO₂Et H 4,5-dihydro-1,2- oxazol-3-yl 1-266 Cl5-(methoxymethyl)- SO₂Et H 5-methyl-4,5- dihydro-1,2-oxazol- 3-yl 1-267Cl CH₂O- SO₂Me H tetrahydrofuran-3-yl 1-268 Cl CH₂O- SO₂Ettetrahydrofuran-3-yl 1-269 Cl CH₂OCH₂- SO₂Me H tetrahydrofuran-2-yl1-270 Cl CH₂OCH₂- SO₂Et H tetrahydrofuran-2-yl 1-271 Cl CH₂OCH₂- SO₂Me Htetrahydrofuran-3-yl 1-272 Cl CH₂OCH₂- SO₂Et H tetrahydrofuran-3-yl1-273 Cl OMe SO₂Me H 1-274 Cl OMe SO₂Et H 1-275 Cl OEt SO₂Me H 1-276 ClOEt SO₂Et H 1-277 Cl O-i-Pr SO₂Me H 1-278 Cl O-i-Pr SO₂Et H 1-279 ClO(CH₂)₂OMe SO₂Me H 1-280 Cl O(CH₂)₄OMe SO₂Me H 1-281 Cl O(CH₂)₄OMe SO₂EtH 1-282 Cl O(CH₂)₃OMe SO₂Me H 1-283 Cl O(CH₂)₃OMe SO₂Et H 1-284 ClO(CH₂)₂OMe SO₂Me H 1-285 Cl O(CH₂)₂OMe SO₂Et H 1-286 Cl [1,4]dioxan-2-SO₂Me H ylmethoxy 1-287 Cl [1,4]dioxan-2- SO₂Et H ylmethoxy 1-288 ClOCH₂(CO)NMe₂ SO₂Me H 1-289 Cl OCH₂(CO)NMe₂ SO₂Et H 1-290 Cl SMe SO₂Me H1-291 Cl SOMe SO₂Me H 1-292 Br OMe Br H 1-293 Br O(CH₂)₂OMe Br H 1-294Br O(CH₂)₂OMe SO₂Me H 1-295 Br O(CH₂)₂OMe SO₂Et H 1-296 Br O(CH₂)₃OMeSO₂Me H 1-297 Br O(CH₂)₃OMe SO₂Et H 1-298 Br O(CH₂)₄OMe SO₂Me H 1-299 BrO(CH₂)₄OMe SO₂Et H 1-300 Br [1,4]dioxan-2- SO₂Me H ylmethoxy 1-301 Br[1,4]dioxan-2- SO₂Et H ylmethoxy 1-302 I O(CH₂)₂OMe SO₂Me H 1-303 IO(CH₂)₂OMe SO₂Et H 1-304 I O(CH₂)₃OMe SO₂Me H 1-305 I O(CH₂)₃OMe SO₂Et H1-306 I O(CH₂)₄OMe SO₂Me H 1-307 I O(CH₂)₄OMe SO₂Et H 1-308 I[1,4]dioxan-2- SO₂Me H ylmethoxy 1-309 I [1,4]dioxan-2- SO₂Et Hylmethoxy 1-310 OMe SMe CF₃ H 1-311 OMe SOMe CF₃ H 1-312 OMe SO₂Me CF₃ H1-313 OMe SOEt CF₃ H 1-314 OMe SO₂Et CF₃ H 1-315 OMe S(CH₂)₂OMe CF₃ H1-316 OMe SO(CH₂)₂OMe CF₃ H 1-317 OMe SO₂(CH₂)₂OMe CF₃ H 1-318 OMe SMeCl H 1-319 OMe SOMe Cl H 1-320 OMe SO₂Me Cl H 1-321 OMe SEt Cl H 1-322OMe SOEt Cl H 1-323 OMe SO2Et Cl H 1-324 OMe S(CH₂)₂OMe Cl H 1-325 OMeSO(CH₂)₂OMe Cl H 1-326 OMe SO₂(CH₂)₂OMe Cl H 1-327 OCH₂c-Pr SMe CF₃ H1-328 OCH₂c-Pr SOMe CF₃ H 1-329 OCH₂c-Pr SO₂Me CF₃ H 1-330 OCH₂c-Pr SEtCF₃ H 1-331 OCH₂c-Pr SOEt CF₃ H 1-332 OCH₂c-Pr SO₂Et CF₃ H 1-333OCH₂c-Pr S(CH₂)₂OMe CF₃ H 1-334 OCH₂c-Pr SO(CH₂)₂OMe CF₃ H 1-335OCH₂c-Pr SO₂(CH₂)₂OMe CF₃ H 1-336 OCH₂c-Pr SMe Cl H 1-337 OCH₂c-Pr SOMeCl H 1-338 OCH₂c-Pr SO₂Me Cl H 1-339 OCH₂c-Pr SEt Cl H 1-340 OCH₂c-PrSOEt Cl H 1-341 OCH₂c-Pr SO₂Et Cl H 1-342 OCH₂c-Pr S(CH₂)₂OMe Cl H 1-343OCH₂c-Pr SO(CH₂)₂OMe Cl H 1-344 OCH₂c-Pr SO₂(CH₂)₂OMe Cl H 1-345OCH₂c-Pr SMe SO₂Me H 1-346 OCH₂c-Pr SOMe SO₂Me H 1-347 OCH₂c-Pr SO₂MeSO₂Me H 1-348 OCH₂c-Pr SEt SO₂Me H 1-349 OCH₂c-Pr SOEt SO₂Me H 1-350OCH₂c-Pr SO₂Et SO₂Me H 1-351 OCH₂c-Pr S(CH₂)₂OMe SO₂Me H 1-352 OCH₂c-PrSO(CH₂)₂OMe SO₂Me H 1-353 OCH₂c-Pr SO₂(CH₂)₂OMe SO₂Me H 1-354 SO₂Me FCF₃ H 1-355 SO₂Me NH₂ CF₃ H 1-356 SO₂Me NHEt Cl H 1-357 SMe SEt F H1-358 SMe SMe F H 1-359 SMe SMe CF₃ H 1-360 SMe SOMe CF₃ H 1-361 SMeSO₂Me CF₃ H 1-362 SMe SMe Cl H 1-363 SMe SMe Br H 1-364 Cl Ac CF₃ H1-365 Cl Ac SO₂Me H 1-366 Cl C(O)cPr CF₃ H 1-367 Cl C(O)cPr SO₂Me H1-368 Cl CH₂SMe CF₃ H 1-369 Cl CH₂S(O)Me CF₃ H 1-370 Cl CH₂SO₂Me CF₃ H1-371 Cl CH₂SMe SO₂Me H 1-372 Cl CH₂S(O)Me SO₂Me H 1-373 Cl CH₂SO₂MeSO₂Me H 1-374 Cl CH═NOMe CF₃ H 1-375 Cl CH═NOMe SO₂Me H 1-376 Cl4,5-dihydro-1,2- CF₃ H oxazol-5-yl, 1-377 Cl 4,5-dihydro-1,2- SO₂Me Hoxazol-5-yl, 1-378 Cl 3-methyl-4,5- CF₃ H dihydro-1,2-oxazol- 5-yl 1-379Cl 3-methyl-4,5- SO₂Me H dihydro-1,2-oxazol- 5-yl 1-380 Cl vinyl CF₃ H1-381 Cl vinyl SO₂Me H 1-382 Cl CO₂Me CF₃ H 1-383 Cl CO₂Me SO₂Me H 1-384Cl SMe CF₃ H 1-385 Cl S(O)Me CF₃ H 1-386 Cl SO₂Me CF₃ H 1-387 Cl SO₂MeSO₂Me H 1-388 Cl SMe Me H 1-389 Cl SOMe Me H 1-390 Cl SO₂Me Me H 1-391Cl 1H-1,2,4-triazol-1-yl CF₃ H 1-392 Cl 1H-1,2,3-triazol-1-yl CF₃ H1-393 Cl 2H-1,2,3-triazol-2-yl CF₃ H 1-394 Cl 1H-pyrazol-1-yl CF₃ H1-395 Cl 1H-4- CF₃ H chloropyrazol-1-yl 1-396 Cl 1H-3- CF₃ Hbromopyrazol-1-yl 1-397 Cl 1H-4- CF₃ H trifluoromethyl- pyrazol-1-yl1-398 Cl pyrolidin-2-on-1-yl CF₃ H 1-399 Cl morpholin-3-on-4-yl CF₃ H1-400 Cl 1,2-thiazolidine- CF₃ H 1,1-dioxid-2-yl 1-401 Br1H-1,2,4-triazol-1-yl CF₃ H 1-402 Br 1H-1,2,4-triazol-1-yl CF₃ H 1-403Br 2H-1,2,3-triazol-2-yl CF₃ H 1-404 Br 1H-pyrazol-1-yl CF₃ H 1-405 Br1H-4- CF₃ H chloropyrazol-1-yl 1-406 Br 1H-3- CF₃ H bromopyrazol-1-yl1-407 Br 1H-4- CF₃ H trifluoromethyl- pyrazol-1-yl 1-408 Brpyrolidin-2-on-1-yl CF₃ H 1-409 Br morpholin-3-on-4-yl CF₃ H 1-410 Br1,2-thiazolidine- CF₃ H 1,1-dioxid-2-yl 1-411 CH₂OMe1H-1,2,4-triazol-1-yl CF₃ H 1-412 CH₂OMe 1H-1,2,4-triazol-1-yl CF₃ H1-413 CH₂OMe 2H-1,2,3-triazol-2-yl CF₃ H 1-414 CF₃ OCH₂CH₂F CF₃ H 1-415CF₃ OMe CF₃ H 1-416 CF₃ SMe CF₃ H 1-417 CF₃ SOMe CF₃ H 1-418 CF₃ SO₂MeCF₃ H 1-419 CF₃ 1H-pyrazol-1-yl CF₃ H 1-420 Me SMe Et H 1-421 Me SOMe EtH 1-422 Me SO₂Me Et H 1-423 Me 1H-pyrazol-1-yl Et H 1-424 Me OCH₂CH₂F EtH 1-425 Me OMe Et H 1-426 Me Ac CF₃ H 1-427 Me Ac SO₂Me H 1-428 MeC(O)cPr CF₃ H 1-429 Me C(O)cPr SO₂Me H 1-430 Me CH₂SMe CF₃ H 1-431 MeCH₂S(O)Me CF₃ H 1-432 Me CH₂SO₂Me CF₃ H 1-433 Me CH₂SMe SO₂Me H 1-434 MeCH₂S(O)Me SO₂Me H 1-435 Me CH₂SO₂Me SO₂Me H 1-436 Me CH═NOMe CF₃ H 1-437Me CH═NOMe SO₂Me H 1-438 Me 4,5-dihydro-1,2- CF₃ H oxazol-5-yl, 1-439 Me4,5-dihydro-1,2- SO₂Me H oxazol-5-yl, 1-440 Me 3-methyl-4,5- CF₃ Hdihydro-1,2-oxazol- 5-yl 1-441 Me 3-methyl-4,5- SO₂Me Hdihydro-1,2-oxazol- 5-yl 1-442 Me vinyl CF₃ H 1-443 Me vinyl SO₂Me H1-444 Me CO₂Me CF₃ H 1-445 Me CO₂Me SO₂Me H 1-446 Me CO₂Me SMe H 1-447Me NH₂ CF₃ H ¹H-NMR (400.0 MHz, CDCl₃): 7.519 (0.7); 7.284 (2.2); 7.260(119.6); 6.996 (0.7); 6.821 (1.9); 6.801 (1.8); 4.281 (2.5); 4.064(15.4); 2.422 (2.3); 2.137 (16.0); 2.045 (2.1); 1.552 (1.7); 1.277(0.7); 1.259 (1.4); 1.241 (0.6); 0.882 (0.7); 0.008 (1.3); 0.000 (39.1);−0.009 (1.1) 1-448 Me NMe₂ CF₃ H ¹H-NMR (400.0 MHz, CDCl₃): 7.468 (0.9);7.448 (1.4); 7.373 (1.2); 7.353 (0.8); 7.260 (55.6); 4.087 (7.4); 2.826(1.4); 2.684 (16.0); 2.520 (0.7); 2.291 (8.3); 1.545 (2.5); 0.008 (0.6);0.000 (19.2); −0.009 (0.5) 1-449 Me NHMe CF₃ H ¹H-NMR (400.0 MHz,CDCl₃): 7.373 (1.7); 7.352 (2.0); 7.261 (33.1); 7.133 (1.7); 7.113(1.5); 4.063 (16.0); 2.729 (10.7); 2.356 (14.5); 1.553 (1.5); 1.256(1.2); 0.000 (12.2) 1-450 Me SO₂Me Me H ¹H-NMR (600.1 MHz, CD₃CN): 7.673(2.0); 7.659 (2.1); 7.298 (1.7); 7.285 (1.6); 4.093 (8.5); 3.043 (16.0);2.628 (12.0); 2.615 (12.0); 2.135 (28.1); 2.103 (0.4); 2.101 (0.5);1.956 (0.4); 1.951 (0.7); 1.948 (3.0); 1.944 (5.3); 1.939 (7.4); 1.935(5.1); 1.931 (2.6); 0.000 (2.7) 1-451 Me SMe Me H 1-452 Me SEt OMe H¹H-NMR (400.1 MHz, CDCl₃): 7.579 (2.4); 7.558 (2.5); 7.260 (34.2); 6.694(2.0); 6.672 (1.9); 4.027 (9.7); 3.876 (16.0); 2.720 (1.4); 2.701 (4.4);2.683 (4.5); 2.665 (1.5); 2.549 (13.8); 1.546 (6.4); 1.256 (1.0); 1.042(4.7); 1.023 (9.8); 1.005 (4.5) 1-453 Me CO₂Et SMe H 7.86 (d, 2H), 7.24(d, 2H), 4.32 (q, 4H), 4.16 (s, 3H), 2.49 (s, 6H), 2.25 (s, 6H), 1.31(t, 6H) 1-454 Me SMe NMe₂ H ¹H-NMR (400.1 MHz, CDCl₃): 7.447 (1.3);7.426 (1.4); 7.262 (8.6); 6.766 (0.7); 6.744 (0.7); 5.298 (0.7); 4.024(6.4); 2.852 (16.0); 2.517 (7.5); 2.131 (12.3) 1-455 Me SMe c-Pr H 7.38(d, 2H), 6.60 (d, 2H), 4.04 (s, 3H), 2.75-2.65 (m, 2H), 2.53 (s, 6H),2.14 (s, 6H), 1.11-1.06 (m, 4H), 0.70-0.67 (m, 4H) 1-456 Me SMe OMe H¹H-NMR (400.1 MHz, CDCl₃): 7.548 (1.6); 7.526 (1.7); 7.262 (11.5); 6.699(1.3); 6.678 (1.2); 4.029 (7.8); 3.903 (11.1); 2.542 (9.1); 2.203 (16.0)1-457 Me SMe OEt H ¹H-NMR (400.1 MHz, CDCl₃): 7.506 (1.6); 7.484 (1.7);7.266 (0.4); 7.2654 (0.5); 7.2645 (0.8); 7.261 (26.5); 7.256 (0.8);7.2554 (0.6); 7.2546 (0.5); 7.254 (0.5); 7.253 (0.4); 7.252 (0.3); 6.665(1.3); 6.643 (1.3); 5.299 (2.2); 4.132 (0.8); 4.124 (0.4); 4.114 (2.6);4.108 (0.5); 4.097 (2.6); 4.079 (0.9); 4.033 (0.5); 4.027 (7.5); 3.995(0.8); 3.788 (1.0); 2.838 (0.4); 2.511 (9.3); 2.494 (0.5); 2.322 (0.9);2.245 (1.4); 2.240 (0.4); 2.229 (0.7); 2.228 (0.7); 2.223 (16.0); 2.193(1.5); 2.153 (0.4); 1.526 (0.4); 1.518 (0.4); 1.509 (0.9); 1.503 (2.9);1.494 (1.1); 1.485 (6.1); 1.477 (0.7); 1.468 (2.8); 1.258 (0.5); 1.256(0.5); 0.000 1-458 Me SMe OCH₂CF₃ H ¹H-NMR (400.0 MHz, d₆-DMSO): 7.789(1.8); 7.767 (1.9); 7.030 (1.4); 7.008 (1.3); 4.901 (0.6); 4.880 (1.7);4.858 (1.8); 4.836 (0.6); 4.145 (7.6); 3.321 (125.9); 3.297 (4.7); 2.706(1.1); 2.524 (0.7); 2.519 (1.0); 2.510 (14.8); 2.506 (32.2); 2.501(45.2); 2.497 (31.5); 2.492 (13.9); 2.427 (9.2); 2.279 (2.2); 2.169(16.0); 0.858 (0.5); 0.000 (5.0) 1-459 Me F SMe H 1-460 Me SMe H Me¹H-NMR (400.1 MHz, CDCl₃): 7.525 (0.4); 7.517 (1.5); 7.309 (1.3); 7.273(0.6); 7.272 (0.6); 7.271 (0.7); 7.258 (264.8); 7.251 (2.7); 7.250(2.5); 7.249 (2.2); 7.2474 (1.7); 7.2466 (1.6); 7.246 (1.4); 7.245(1.3); 7.244 (1.1); 7.2433 (1.1); 7.2425 (1.0); 7.242 (0.9); 7.241(0.9); 7.240 (0.8); 7.2393 (0.7); 7.2385 (0.7); 7.238 (0.6); 7.237(0.6); 7.235 (0.5); 7.234 (0.5); 7.233 (0.4); 7.232 (0.4); 7.229 (0.4);7.177 (0.5); 7.024 (1.7); 6.994 (1.5); 6.945 (1.7); 4.072 (10.7); 2.574(2.3); 2.462 (4.6); 2.372 (16.0); 2.359 (2.4); 2.358 (2.4); 2.305 (7.5);2.304 (7.8); 2.155 (8.8); 1.529 (3.4); 1.258 (1.2); 0.051 (0.4); 0.011(0.5); 0.008 (2.7); 0.000 (86.3) 1-461 Me NO₂ H Br 1-462 Et SMe Br H1-463 Et SEt Cl H 1-464 Et SOMe CF₃ H 1-465 Et SOMe Cl H 1-466 Et SEtCF₃ H 1-467 Et SOEt CF₃ H 1-468 Et SO₂Et CF₃ H 1-469 OMe CH₂OMe Cl H1-470 OMe CH₂-2H-tetrazol-2- Cl H 8.50 (s, 2H), 7.59 (d, 2H), 7.30 yl(d, 2H), 6.06 (s, 2H), 4.02 (s, 3H), 3.93 (s, 6H) 1-471 OEt SMe CF₃ H¹H-NMR (400.0 MHz, CDCl₃): 7.616 (1.1); 7.615 (1.1); 7.595 (2.3); 7.559(3.3); 7.539 (1.6); 7.260 (21.7); 5.298 (1.1); 4.267 (1.1); 4.249 (3.5);4.231 (3.6); 4.214 (1.1); 4.119 (11.8); 2.307 (16.0); 1.495 (4.7); 1.477(10.2); 1.459 (4.5); 0.000 (7.1) 1-472 OEt SO₂Me CF₃ H ¹H-NMR (400.0MHz, CDCl₃): 7.897 (0.6); 7.876 (4.3); 7.870 (5.5); 7.849 (0.8); 7.520(0.6); 7.294 (0.6); 7.268 (0.7); 7.266 (1.1); 7.261 (109.0); 6.997(0.6); 4.237 (0.9); 4.220 (2.8); 4.202 (2.9); 4.185 (0.9); 4.154 (13.5);3.191 (16.0); 1.566 (4.3); 1.548 (13.4); 1.531 (4.4); 4.284 (0.8); 1.259(1.8); 0.880 (0.7); 0.008 (1.5); 0.000 (48.2); 0.009 (1.3) 1-473 ClS-nPr CF₃ H 1-474 Cl SOEt CF₃ H 1-475 Cl SO₂Et CF₃ H 1-476 Cl Vinyl SMeH 1-477 Cl CH₂OMe OMe H ¹H-NMR (400.0 MHz, CDCl₃): 7.596 (2.2); 7.574(2.3); 7.260 (50.1); 6.811 (1.7); 6.789 (1.7); 4.557 (6.1); 4.060 (7.2);3.868 (11.6); 3.325 (16.0); 1.537 (1.9); 1.256 (0.5); 0.008 (0.6); 0.000(18.8); −0.009 (0.6) 1-478 Cl CH₂OMe SMe H 1-479 Cl C(O)-c-Pr Me H 7.47(d, 2H), 7.17 (d, 2H), 4.09 (s, 3H), 2.26 (s, 6H), 2.12-2.07 (m, 2H),1.32-1.29 (m, 4H), 1.15-1.10 (m, 4H) 1-480 Cl CH(OMe)-i-Pr Cl H 1-481 ClCH₂O—N═CH₂ Cl H 1-482 Cl CH₂O—N═CHMe Cl H 1-483 Cl CH₂O—N═CMe₂ Cl H1-484 Cl [diethyl(oxido)- Cl H lambda⁶- sulfanylidene]amino 1-485 Cl(4-oxido- Cl H 1,4lambda⁴- oxathian-4- ylidene)amino 1-486 Cl2-methylpyridin-3-yl Me H 1-487 Cl 3-methyl-4,5- SMe H ¹H-NMR (400.0MHz, CDCl₃): dihydro-1,2-oxazol- 7.519 (2.0); 7.460 (1.8); 7.451 5-yl(1.9); 7.440 (2.8); 7.430 (2.7); 7.368 (2.1); 7.344 (2.4); 7.323 (1.6);7.310 (0.7); 7.294 (3.5); 7.260 (390.8); 7.229 (0.6); 6.996 (2.1); 6.503(0.8); 6.492 (0.8); 6.474 (1.7); 6.462 (1.6); 6.445 (0.8); 6.433 (0.8);4.169 (7.9); 4.161 (7.9); 4.131 (0.7); 4.113 (0.6); 3.259 (2.4); 3.232(2.1); 2.349 (15.7); 2.344 (15.3); 2.091 (16.0); 2.045 (2.5); 2.007(2.1); 1.544 (10.2); 1.277 (0.7); 1.259 (1.6); 1.241 (0.8); 0.034 (1.2);0.008 (3.9); 0.000 (123.9); −0.009 (3.5) 1-488 Cl SEt CF₃ H 1-489 Cl MeF Me 7.55 (d, 2H), 4.18 (s, 3H), 2.20 (d, 6H), 2.16 (d, 6H) 1-490 Cl H FMe ¹H-NMR (400.0 MHz, CDCl₃): 7.519 (2.0); 7.460 (1.8); 7.451 (1.9);7.440 (2.8); 7.430 (2.7); 7.368 (2.1); 7.344 (2.4); 7.323 (1.6); 7.310(0.7); 7.294 (3.5); 7.260 (390.8); 7.229 (0.6); 6.996 (2.1); 6.503(0.8); 6.492 (0.8); 6.474 (1.7); 6.462 (1.6); 6.445 (0.8); 6.433 (0.8);4.169 (7.9); 4.161 (7.9); 4.131 (0.7); 4.113 (0.6); 3.259 (2.4); 3.232(2.1); 2.349 (15.7); 2.344 (15.3); 2.091 (16.0); 2.045 (2.5); 2.007(2.1); 1.544 (10.2); 1.277 (0.7); 1.259 (1.6); 1.241 (0.8); 0.034 (1.2);0.008 (3.9); 0.000 (123.9); −0.009 (3.5) 1-491 Br CH₂OMe SO₂Me H 1-492Br F CF₃ H 1-493 Br 1H-pyazol-1-yl Cl H 1-494 I SMe H Me 1-495 CH₂OMeSMe CF₃ H 1-496 CH₂OMe SCH₂CH₂OMe CF₃ H 1-497 c-Pr SOMe CF₃ H 1-498 c-PrSMe Et H ¹H NMR (400 MHz, CDCl₃): 7.260 (29.5); 7.230 (1.1); 7.210(1.5); 7.104 (1.4); 7.084 (1.1); 4.025 (7.7); 2.960 (0.7); 2.941 (2.1);2.922 (2.2); 2.904 (0.7); 2.322 (16.0); 2.149 (0.6); 1.535 (1.0); 1.398(0.7); 1.224 (3.2); 1.206 (7.2); 1.187 (3.1); 1.158 (1.1); 1.154 (1.2);1.143 (0.5); 1.137 (1.1); 1.133 (1.1); 0.949 (1.0); 0.945 (1.3); 0.934(1.1); 0.000 (12.8) 1-499 SMe vinyl Cl H 1-500 SMe 3-methyl-4,5- Cl Hdihydro-1,2-oxazol- 5-yl 1-501 SO₂Me 1H-pyrazol-1-yl Cl H 8.63-8.38(broad; 2H); 8.27 (s, broad, 2H), 8.09 (s broad, 2H), 7.89 (s broad,2H), 6.58 (s broad, 2H), 4.17 (s, 3H), 3.31 (s, 6H); 1-502 SO₂Me1H-pyrazol-1-yl CF₃ H 8.31-7.96 (broad; 4H); 7.88- 7.65 (broad, 4H),6.55 (s broad, 2H), 4.23 (s, 3H), 3.27 (s, 6H); 1-503 SO₂Me1H-pyrazol-1-yl OMe H 8.49-7.89 (broad; 4H); 7.85- 7.39 (broad, 4H),6.55 (s, 2H), 4.15 (s, 3H), 3.84 (s, 6H); 3.29 (s, 6H). 1-504 SO₂Me1H-pyrazol-1-yl Me H 8.09-7.73 (m; 8H); 6.58 (s, 2H), 4.16 (s, 3H), 3.31(s, 6H); 3.08 (s, 6H). 1-505 SO₂Me 1H-pyrazol-1-yl 1H-pyrazol-1-yl H

TABLE 2 Inventive compounds of the formula (I) in which Q is Q1, W isC—Y, R is substituted phenyl and R⁶ is ethyl. Table 2 contains 454compounds (2-1 to 2-454) in which X, Y and Z are as defined in examples1-1 to 1-454 of table 1, and examples cited hereinafter:

Physical data (¹H-NMR, DMSO-d₆, No. X Y Z V 400 MHz) 2- Me SMe H Me 7.02(s, 2H), 6.93 (s, 2H), 460 4.33 (q, 2H), 2.35 (s, 6H), 2.30 (s, 6H),2.14 (s, 6H), 1.68 (t, 3H) 2- Me NO₂ H Br ¹H-NMR (400.0 MHz, CDCl₃): 4618.292 (2.4); 8.287 (2.5); 8.106 (0.6); 8.101 (0.7); 8.039 (0.6); 8.034(0.5); 8.017 (2.4); 8.012 (2.2); 7.259 (72.2); 4.553 (1.0); 4.535 (1.0);3.501 (0.8); 2.610 (16.0); 2.576 (5.0); 1.684 (1.5); 1.666 (3.2); 1.647(1.5); 0.008 (0.8); 0.000 (26.9); −0.009 (0.8) 2- Et SEt Cl H ¹H-NMR(400.0 MHz, CDCl₃): 463 7.393 (3.5); 7.372 (6.0); 7.317 (6.6); 7.296(3.9); 7.260 (81.7); 4.309 (1.1); 4.291 (3.5); 4.273 (3.6); 4.254 (1.1);2.988 (1.1); 2.969 (3.6); 2.951 (3.7); 2.932 (1.2); 2.830 (2.1); 2.811(7.1); 2793 (7.2); 2.774 (2.3); 2.044 (0.5); 1.689 (3.7); 1.671 (8.1);1.653 (3.6); 1.551 (1.3); 1.259 (0.8); 1.256 (0.8); 1.234 (4.6); 1.216(11.1); 1.197 (5.4); 1.195 (8.9); 1.176 (16.0); 1.158 (7.3); 0.008(0.8); 0.000 (26.8); −0.009 (0.9) 2- Cl CH₂OMe OMe H ¹H-NMR (400.0 MHz,CDCl₃): 477 7.607 (2.1); 7.586 (2.3); 7.260 (91.8); 6.996 (0.5); 6.799(1.6); 6.777 (1.6); 5.298 (0.7); 4.552 (5.7); 4.342 (1.5); 4.323 (1.5);3.863 (11.0); 3.322 (16.0); 2.101 (2.1); 1.649 (1.6); 1.631 (3.5); 1.613(1.6); 1.536 (1.5); 1.256 (0.8); 0.008 (1.1); 0.000 (35.0); −0.009 (1.0)2- Cl CH(OMe)-i-Pr Cl H ¹H-NMR (400.0 MHz, CDCl₃): 480 7.519 (1.0);7.409 (3.1); 7.389 (9.0); 7.367 (5.5); 7.346 (2.0); 7.260 (190.6); 7.253(0.8); 6.996 (1.0); 4.594 (1.3); 4.348 (1.4); 4.331 (1.4); 3.137 (6.9);2.495 (0.6); 2.005 (0.5); 1.690 (7.1); 1.671 (15.7); 1.653 (7.1); 1.256(0.8); 1.149 (16.0); 1.132 (15.5); 0.655 (5.0); 0.639 (5.2); 0.008(2.3); 0.007 (0.8); 0.006 (0.9); 0.005 (1.0); 0.004 (1.4); 0.000 (66.8);−0.005 (0.7); −0.006 (0.5); −0.008 (1.7) 2- SMe vinyl Cl H ¹H-NMR (400.0MHz, CDCl₃); 499 7.402 (1.7); 7.381 (2.3); 7.266 (2.0); 7.260 (17.6);7.246 (1.4); 6.846 (0.8); 6.815 (0.6); 6.803 (0.6); 6.772 (0.9); 5.754(5.2); 5.727 (1.4); 5.724 (1.8); 5.711 (1.7); 5.708 (1.3); 4.519 (0.5);4.500 (1.7); 4.482 (1.7); 4.464 (0.5); 2.274 (16.0); 1.672 (1.8); 1.654(4.0); 1.636 (1.8); 1.542 (1.6); 0.0000 (6.1) 2- SMe 3-methyl-4,5- Cl H¹H-NMR (400.0 MHz, CDCl₃): 500 dihydro-1,2- 7.445 (1.7); 7.434 (1.9);7.425 oxazol-5-yl (2.7); 7.413 (2.7); 7.361 (1.7); 7.340 (1.2); 7.334(1.8); 7.313 (1.3); 7.261 (76.7); 7.228 (0.7); 6.504 (0.8); 6.488 (0.8);6.475 (1.7); 6.459 (1.5); 6.446 (0.8); 6.430 (0.8); 4.484 (1.1); 4.470(1.7); 4.466 (1.3); 4.451 (1.6); 3.260 (2.1); 3.258 (2.1); 3.235 (1.7);3.227 (1.9); 2.342 (15.5); 2.336 (14.9): 2.092 (16.0); 2.045 (0.8);1.674 (1.9); 1.670 (2.0); 1.656 (4.4); 1.652 (4.4); 1.637 (2.0); 1.633(2.0); 1.259 (0.6); 0.008 (0.7); 0.000 (22.1); −0.009 (0.6)

TABLE 3 Inventive compounds of the formula (I) in which Q is Q2, W isC—Y, R is substituted phenyl and R⁷ is methyl. Table 3 contains 454compounds (3- 1 to 3-454) in which X, Y and Z are as defined in examples1-1 to 1-454 of table 1, and examples cited hereinafter:

Physical data No. X Y Z V (¹H-NMR, DMSO-d₆, 400 MHz) 3-95 Me F SMe H7.95 (s, 1H), 7.63 (d, 2H), 7.19 (dd, 2H), 3.86 (s, 3H), 2.50 (s, 6H),2.24 (d, 6H) 3-143 Me SMe CF₃ H 7.99 (s, 1H), 7.94 (d, 2H), 7.71 (d,2H), 3.95 (s, 3H), 2.64 (s, 6H), 2.22 (d, 6H) 3-146 Me SEt CF₃ H ¹H-NMR(400.1 MHz, CDCl₃): 7.757 (4.6); 7.602 (1.7); 7.582 (2.5); 7.520 (0.4);7.489 (2.2); 7.469 (1.6); 7.272 (0.3); 7.271 (0.4); 7.270 (0.5); 7.269(0.7); 7.2683 (0.8); 7.2675 (1.0); 7.267 (1.2); 7.261 (75.4); 7.2534(0.8); 7.2526 (0.7); 7.252 (0.7); 7.251 (0.6); 7.250 (0.5); 7.249 (0.5);7.248 (0.4); 7.247 (0.4); 7.246 (0.3); 6.998 (0.4); 3.868 (13.3); 2.899(1.4); 2.757 (0.4); 2.738 (16.0); 2.716 (1.3); 2.697 (3.7); 2.679 (3.8);2.660 (1.3); 1.561 (1.0: 1.233 (0.5); 1.215 (1.0); 1.201 (5.0); 1.182(10.3); 1.164 (4.8); 0.008 (0.8); 0.006 (0.4); 0.005 (0.5); 0.004 (0.7)3-202 Et SMe CF₃ H 3-470 OMe CH₂-2H-tetrazol-2- Cl H 8.49 (s, 2H), 7.76(s, 1H), yl 7.58 (d, 2H), 7.28 (d, 2H), 5.91 (s, 2H), 3.93 (s, 6H), 3.79(s, 3H) 3-475 Cl SO₂Et CF₃ H ¹H-NMR (400.0 MHz, CDCl₃): 7.985 (2.4);7.964 (3.0); 7.797 (2.2); 7.776 (1.9); 7.744 (5.8); 7.267 (0.8); 7.261(71.7); 4.148 (0.6); 4.131 (1.7); 4.113 (1.7); 4.095 (0.6); 3.940(16.0); 3.923 (0.7); 3.867 (0.7); 3.835 (0.6); 3.500 (1.7); 3.481 (5.6);3.462 (5.7); 3.444 (1.8); 2.097 (0.6); 2.045 (8.1); 1.455 (0.5); 1.450(0.5); 1.438 (5.8); 1.419 (12.6); 1.401 (5.5); 1.277 (2.6); 1.266 (1.0);1.259 (5.3); 1.241 (2.4); 0.882 (1.7); 0.864 (0.6); 0.008 (1.0); 0.000(30.6); −0.009 (0.9) 3.476 Cl vinyl SMe H ¹H-NMR (400.0 MHz, CDCl₃):7.876 (3.7); 7.434 (2.2); 7.433 (2.2); 7.413 (2.3); 7.412 (2.4); 7.261(24.0); 6.999 (2.4); 6.978 (2.2); 6.519 (1.1); 6.490 (1.2); 6.474 (1.2);6.446 (1.3); 5.737 (2.4); 5.734 (2.5); 5.708 (2.3); 5.705 (2.4); 5.564(2.5); 5.561 (2.4); 5.519 (2.3); 5.516 (2.2); 3.908 (12.0); 2.416(16.0); 1.255 (0.8); 0.000 (7.3) 3-477 Cl CH₂OMe OMe H ¹H-NMR (400.0MHz, CDCl₃): 7.804 (2.4); 7.602 (2.0); 7.581 (2.1); 7.268 (0.5); 7.2674(0.6); 7.2666 (0.7); 7.266 (0.8); 7.265 (1.0); 7.259 (75.8); 7.255(0.8); 7.254 (0.5); 6.802 (1.4); 6.780 (1.4); 5.298 (0.9); 4.576 (5.0);3.873 (6.8); 3.865 (10.0); 3.325 (16.0); 1.536 (7.0); 0.008 (0.9); 0.000(30.4); −0.009 (0.9) 3-479 Cl C(O)-c-Pr Me H 7.84 (s, 1H), 7.47 (d, 2H),7.15 (d, 2H), 3.89 (s, 3H), 3.25 (s, 6H), 2.14-2.10 (m, 2H), 1.32-1.28(m, 4H), 1.14- 1.09 (m, 4H) 3-480 Cl CH(OMe)-i-Pr Cl H Example 3-480:¹H-NMR (400.0 MHz, CDCl₃): 7.689 (4.9); 7.519 (0.7); 7.385 (1.6); 7.365(3.9); 7.350 (0.6); 7.340 (4.9); 7.319 (2.0); 7.260 (127.0); 6.996(0.7); 4.634 (1.0); 4.612 (1.1); 3.905 (7.4); 3.154 (13.8); 2.534 (0.6);1.154 (16.0); 1.138 (15.6); 0.659 (3.7); 0.646 (3.9); 0.008 (1.3); 0.000(44.3); −0.009 (1.3) 3-486 Cl 2-methylpyridin-3-yl Me H Example 3-486;¹H-NMR (400.0 MHz, CDCl₃): 8.606 (1.7); 8.593 (1.7); 7.764 (3.7); 7.756(3.3); 7.519 (0.9); 7.514 (2.2); 7.509 (1.8); 7.494 (2.6); 7.489 (2.2);7.350 (1.4); 7.334 (1.9); 7.300 (1.9); 7.311 (0.6); 7.284 (3.4); 7.274(2.3); 7.261 (125.8); 7.244 (1.1); 6.997 (0.7); 3.939 (2.5); 3.908(1.1); 3.873 (14.3); 2.320 (1.4); 2.298 (1.8); 2.271 (0.6); 2.218 (7.8);2.206 (8.0); 2.140 (0.6); 2.089 (0.5); 2.061 (1.1); 2.038 (1.9); 2.032(1.6); 2.013 (16.0); 0.008 (1.6); 0.000 (45.1); −0.009 (1.1) 3-487 Cl3-methyl-4,5- SMe H ¹H-NMR (400.0 MHz, CDCl₃): dihydro-1,2-oxazol- 7.926(3.8); 7.912 (3.8); 5-yl 7.522 (0.6); 7.463 (3.0); 7.453 (2.9); 7.442(3.5); 7.433 (3.2); 7.273 (0.5); 7.272 (0.6); 7.269 (1.0); 7.263(115.7); 7.104 (3.5); 7.083 (3.1); 6.999 (0.6); 6.152 (1.0); 6.141(1.0); 6.123 (2.4); 6.112 (2.5); 6.093 (1.0); 6.082 (1.0); 4.131 (0.8);4.113 (0.8); 3.954 (1.0); 3.928 (0.6); 3.922 (10.8); 3.919 (10.7); 3.910(0.5); 3.181 (0.9); 3.178 (1.0); 3.172 (1.1); 3.170 (1.1); 3.162 (1.1);3.160 (1.1); 3.149 (1.8); 3.143 (1.2); 3.140 (1.1); 3.132 (1.1); 3.130(1.0); 3.121 (1.0); 3.119 (1.1); 2.483 (15.7); 2.481 (16.0); 2.473(1.6); 2.468 (0.8); 2.465 (0.9); 2.348 (0.5); 2.336 (0.5); 2.094 (1.7);2.075 (12.2); 2.072 (12.0); 2.045 (3.9); 1.583 (1.1); 1.333 (0.5); 1.284(0.8); 1.277 (1.3); 1.259 (4.1); 1.243 (1.4); 1.241 (1.3); 1.226 (0.7);0.880 (0.7); 0.008 (0.6); 0.000 (24.6); −0.009 (0.7) 3-490 Cl H F Me7.99 (s, 1H), 7.72 (d, 2H), 7.47 (d, 2H), 3.90 (s, 3H), 2.23 (s, 6H)3-491 Br CH₂OMe SO₂Me H 3-492 Br F CF₃ H ¹H-NMR (400.0 MHz, CDCl₃):7.775 (1.7); 7.428 (0.5); 7.2674 (0.5); 7.2666 (0.6); 7.266 (0.7); 7.265(0.9); 7.264 (1.2); 7.260 (71.3); 7.255 (0.5); 3.957 (5.7); 1.539(16.0); 0.008 (0.8); 0.000 (27.8); −0.009 (0.8) 3-493 Br 1H-pyrazol-1-ylCl H 7.84 (d, 2H), 7.81 (s, 1H), 7.60 (d, 2H), 7.56 (d, 2H), 7.53 (d,2H), 6.53 (t, 2H), 3.91 (s, 3H), 3-494 I SMe H Me ¹H-NMR (400.1 MHz,CDCl₃): 7.881 (3.1); 7.518 (1.2); 7.309 (0.5); 7.2803 (0.3); 7.2795(0.4); 7.279 (0.4); 7.278 (0.4); 7.277 (0.4); 7.2763 (0.5); 7.2755(0.5); 7.275 (0.5); 7.274 (0.6); 7.273 (0.6); 7.272 (0.7); 7.2714 (0.8);7.2705 (0.9); 7.270 (1.0); 7.269 (1.1); 7.268 (1.3); 7.2673 (1.4);7.2665 (1.8); 7.266 (2.1); 7.265 (2.8); 7.264 (3.6); 7.263 (4.7); 7.260(208.2); 7.254 (4.4); 7.253 (3.7); 7.2523 (3.1); 7.2515 (2.6); 7.251(2.2); 7.250 (2.0); 7.249 (1.6); 7.248 (1.5); 7.2474 (1.3); 7.2466(1.2); 7.246 (1.0); 7.245 (1.0); 7.244 (0.9); 7.2433 (0.8); 7.2425(0.7); 7.242 (0.7); 7.241 (0.6); 7.240 (0.6); 7.239 (0.5); 7.2384 (0.4);7.2376 (0.4); 7.237 (0.4); 7.236 (0.4); 7.235 (0.4); 7.2343 (0.4);7.2336 (0.4); 7.104 (1.7); 7.101 (1.8); 6.996 (1.2); 6.824 (1.7); 6.820(1.7); 4.113 (0.3); 3.973 (10.2); 3.887 (0.4); 2.435 (0.4); 2.425 (0.5);2.408 (16.0); 2.332 (11.1); 2.043 (1.6); 1.540 (91.4); 1.276 (0.6);1.264 (0.4); 1.258 (1.1); 1.240 (0.5); 0.882 (0.7); 0.008 (1.9) 3-495CH₂OMe SMe CF₃ H ¹H-NMR (400.0 MHz, CDCl₃): 7.722 (2.6); 7.681 (1.2);7.660 (2.0); 7.606 (1.5); 7.585 (0.9); 7.261 (24.0); 5.299 (1.1); 5.114(5.9); 3.849 (8.0); 3.369 (16.0); 2.251 (12.5); 1.371 (1.1); 1.333(1.2); 1.285 (2.3); 1.256 (2.9); 0.000 (9.1) 3-500 SMe 3-methyl-4,5- ClH ¹H-NMR (400.0 MHz, CDCl₃): dihydro-1,2-oxazol- 7.775 (2.6); 7.759(2.3); 5-l 7.520 (0.5); 7.438 (1.9); 7.432 (1.7); 7.418 (3.1); 7.411(2.5); 7.359 (2.0); 7.339 (2.4); 7.319 (1.0); 7.261 (90.4); 6.542 (0.7);6.531 (0.8); 6.513 (1.8); 6.501 (1.5); 6.484 (0.8); 6.473 (0.8); 3.971(7.1); 3.966 (8.5); 3.268 (2.1); 3.239 (1.9); 3.229 (1.2); 2.458 (1.0);2.348 (12.9); 2.342 (14.9); 2.133 (0.9); 2.101 (1.1); 2.089 (16.0);2.045 (0.7); 1.560 (1.0); 1.259 (0.8); 0.008 (0.9); 0.000 (26.7); −0.009(0.7)

TABLE 4 Inventive compounds of the formula (I) in which Q is Q3, W isC—Y, R is substituted phenyl and R⁸ is methyl. Table 4 contans 454compounds (4- 1 to 4-454 ) in which X, Y and Z are as defined inexamples 1-1 to 1-454 of table 1.

Physical data (¹H-NMR, DMSO-d₆, 400 Nr. X Y Z V MHz) 4-35 NO₂ H F H 8.26(dd, 2H), 7.99 (dd, 2H), 7.88 (dd, 2H), 1.52 (s, 3H) 4-36 NO₂ H Cl H8.22 (dd, 2H), 7.73 (dd, 2H), 7.49 (d, 2H), 2.48 (s, 3H) 4-144 Me SOMeCF₃ H 7.61 (2d, 2H), 7.49 (2d, 2H), 2.96 (s, 6H), 2.93 (s, 6H), 2.41 (s,3H) 4-157 Me NH₂ SO₂Me H 7.45 (d, 2H), 6.98 (d, 2H), 5.99 (s, 4H), 3.10(s, 6H), 2.45 (s, 3H), 1.99 (s, 6H) 4-185 Me SO₂Me SO₂Me H 8.37 (d, 2H),8.18 (d, 2H), 3.56 (s, 6H), 3.51 (s, 6H), 2.69 (s, 3H) 4-187 Me SEtSO₂Me H ¹H-NMR (400.1 MHz, CDCl₃): 8.121 (2.2); 8.101 (2.4); 7.520(0.7); 7.518 (0.7); 7.464 (2.6); 7.443 (2.5); 7.268 (0.5); 7.267 (0.6);7.261 (114.8); 7.259 (126.6); 7.251 (1.3); 7.250 (1.1); 7.249 (1.0);7.2484 (0.9); 7.2476 (0.8); 7.247 (0.7); 7.246 (0.6); 7.245 (0.5);7.2443 (0.5); 7.2435 (0.5); 7.243 (0.4); 7.242 (0.4); 7.241 (0.4); 7.240(0.4); 7.239 (0.3); 6.997 (0.7); 6.996 (0.7); 5.298 (0.7); 3.506 (0.5);3.486 (0.5); 3.436 (16.0); 3.047 (0.3); 2.921 (0.3); 2.911 (1.2); 2.893(3.8); 2.874 (3.9); 2.856 (1.3); 2.739 (13.3); 2.628 (0.4); 2.433 (7.9);2.432 (8.1); 1.532 (44.2); 1.531 (47.6); 1.312 (0.4); 1.280 (4.1); 1.261(8.3); 1.243 (3.9); 0.010 (1.3); 0.008 (1.6); 0.001 (47.4); 0.000 (52.7)4-188 Me SOEt SO₂Me H ¹H-NMR (400.1 MHz, CDCl₃): 8.105 (1.8); 8.085(2.0); 8.045 (1.3); 8.025 (1.5); 7.584 (2.3); 7.564 (2.1); 7.414 (2.3);7.394 (2.1); 7.261 (31.7); 3.442 (16.0); 3.418 (0.8); 3.399 (0.3); 3.395(0.4); 3.338 (12.4); 3.242 (0.7); 3.223 (0.8); 3.210 (0.6); 3.190 (0.6);2.908 (6.3); 2.890 (1.9); 2.879 (1.7); 2.871 (1.7); 2.861 (1.6); 2.852(0.7); 2.842 (0.5); 2.832 (0.4); 2.726 (11.6); 2.437 (15.9); 2.043(1.3); 1.552 (10.7); 1.53 7(3.2); 1.518 (6.6); 1.499 (3.0); 1.273 (4.0);1.254 (8.5); 1.236 (3.7); 0.008 (0.5) 4-199 CH₂O(CH₂)₂OMe NH(CH₂)₃OMeSO₂Me H 7.74 (d, 2H), 7.12 (d, 2H), 4.63 (s, 4H), 3.59-3.47 (m, 12H),3.39 (s, 6H), 3.35 (s, 6H), 3.26 (t, 4H), 3.09 (s, 6H), 2.45 (s, 3H),1.94-1.87 (m, 4H) 4-201 Et SO₂Me Cl H ¹H-NMR (400.1 MHz, CDCl₃): 7.494(2.1); 7.474 (3.3); 7.406 (3.0); 7.385 (1.9); 7.262 (8.9); 5.299 (5.8);3.352 (0.6); 3.342 (16.0); 3.263 (0.6); 3.244 (1.7); 3.226 (1.7); 3.208(0.6); 2.413 (8.1); 2.043 (1.3); 1.550 (2.5); 1.325 (2.7); 1.307 (6.2);1.288 (2.7); 1.276 (0.5); 1.258 (0.8); 1.240 (0.4); 0.000 (3.8) 4-205 EtNH(CH₂)₂OMe SO₂Me H 7.79 (d, 2H), 6.96 (d, 2H), 3.60 (t, 4H), 3.40 (s,6H), 3.38 (t, 4H), 3.20 (s, 6H), 2.75 (q, 4H), 2.40 (s, 3H), 1.21 (t,6H) 4-358 SMe SMe F H 7.30 (dd, 2H), 7.07 (dd, 2H), 2.50 (s, 6H), 2.48(s, 3H), 2.39 (s, 6H) 4-430 Me CH₂SMe CF₃ H ¹H-NMR (400.0 MHz, CDCl₃):7.506 (1.6); 7.485 (2.0); 7.337 (1.8); 7.317 (1.4); 7.265 (0.6); 7.264(0.8); 7.263 (1.0); 7.260 (45.6); 3.805 (5.7); 2.608 (0.6); 2.540 (14.0:2.424 (14.9); 2.387 (0.6); 2.189 (0.5); 2.163 (0.8); 2.115 (16.0); 1.535(5.3); 0.008 (0.5); 0.000 (18.7) 4-448 Me NMe₂ CF₃ H ¹H-NMR (400.0 MHz,CDCl₃): 7.454 (1.0); 7.433 (1.2); 7.301 (1.1); 7.281 (0.9); 7.260(35.3); 2.692 (16.0); 2.430 (8.0); 2.287 (8.3); 1.539 (14.4); 0.000(12.0) 4-449 Me NHMe CF₃ H ¹H-NMR (400.0 MHz, CDCl₃): 7.364 (2.0); 7.343(2.2); 7.260 (43.3); 7.067 (1.9); 7.047 (1.7); 2.736 (13.1); 2.421(14.5); 2.352 (16.0: 1.543 (0.8); 1.255 (1.0); 0.000 (14.9) 4-451 Me SMeMe H ¹H-NMR (400.0 MHz, CDCl₃): 7.302 (1.4); 7.2683 (1.7); 7.260 (14.1);7.073 (1.2); 7.053 (1.0); 2.554 (8.7); 2.497 (8.1); 2.404 (8.4); 2.243(0.7); 2.090 (16.0); 1.546 (1.7); 1.366 (0.8); 0.000 (4.8) 4-452 Me SEtOMe H 7.48 (d, 2H), 6.66 (d, 2H), 3.88 (s, 6H), 2.69 (q, 4H), 2.51 (s,6H), 2.39 (s, 3H), 1.01 (t, 6H) 4-457 Me SMe OEt Me ¹H-NMR (400.1 MHz,CDCl₃): 7.396 (1.7); 7.374 (1.8); 7.265 (0.4); 7.260 (16.4); 6.647(1.3); 6.625 (1.3); 5.298 (1.1); 4.125 (0.8); 4.107 (2.5); 4.090 (2.6);4.072 (0.8); 2.696 (0.8); 2.522 (0.4); 2.505 (0.4); 2.495 (9.4); 2.481(1.3); 2.396 (1.5); 2.392 (7.8); 2.383 (0.4); 2.357 (1.4); 2.325 (0.5);2.248 (0.5); 2.231 (0.7); 2.228 (0.4); 2.221 (16.0); 1.528 (0.6); 1.510(0.4); 1.500 (2.9); 1.492 (0.5); 1.482 (6.3); 1.465 (2.8) 4-460 Me SMe HMe 4-466 Et SEt CF₃ H ¹H-NMR (400.0 MHz, CDCl₃): 7.607 (2.9); 7.586(3.5); 7.392 (2.4); 7.372 (2.0); 7.260 (39.8); 3.143 (1.0); 3.124 (3.5);3.106 (3.6); 3.087 (1.1); 2.745 (1.4); 2.726 (4.5); 2.708 (4.6); 2.689(1.5); 2.415 (16.0); 1.538 (14.0); 1.292 (4.5); 1.273 (10.9); 1.255(4.9); 1.251 (6.6); 1.232 (12.3); 1.213 (5.6); 0.008 (0.5); 0.000(17.2); −0.009 (0.5) 4-469 OMe CH₂OMe Cl H 7.42 (d, 2H), 7.35 (d, 2H),4.38 (s, 4H), 3.92 (s, 6H), 3.40 (s, 6H), 2.42 (s, 3H) 4-470 OMeCH₂-2H-tetrazol-2- Cl H 8.49 (s, 2H), 7.53 (d, 2H), yl 7.26 (d, 2H),5.85 (s, 4H), 3.93 (s, 6H), 2.39 (s, 3H) 4-471 OEt SMe CF₃ H 7.51 (d,2H), 7.49 (d, 2H), 4.22 (q, 4H), 2.44 (s, 3H), 2.30 (s, 6H), 1.46 (t,6H) 4-477 Cl CH₂OMe OMe H ¹H-NMR (400.0 MHz, CDCl₃): 7.540 (2.1); 7.519(2.4); 7.260 (30.9); 6.805 (1.5); 6.783 (1.4); 4.565 (5.4); 3.866(10.5); 3.326 (16.0); 2.419 (7.1); 1.539 (1.2); 0.000 (11.9) 4-481 ClCH₂O—N═CH₂ Cl H 4-482 Cl CH₂O—N═CHMe Cl H 4-483 Cl CH₂O—N═CMe₂ Cl H4-487 Cl 3-methyl-4,5- SMe H ¹H-NMR (400.0 MHz, CDCl₃):dihydro-1,2-oxazol- 7.520 (0.7); 7.414 (2.6); 7.401 5-yl (2.3); 7.393(3.0); 7.380 (2.6); 7.273 (0.5); 7.2724 (0.5); 7.2716 (0.6); 7.271(0.7); 7.270 (0.7); 7.269 (0.9); 7.2684 (1.1); 7.2676 (1.2); 7.267(1.4); 7.266 (1.7); 7.265 (2.3); 7.261 (126.8); 7.083 (3.0); 7.063(2.6); 6.997 (0.7); 6.137 (0.8); 6.129 (0.9); 6.108 (2.0); 6.099 (2.1);6.078 (0.9); 6.070 (0.9); 4.149 (1.1); 4.131 (3.3); 4.113 (3.4); 4.095(1.1); 3.175 (0.8); 3.166 (0.8); 3.159 (0.9); 3.146 (1.5); 3.139 (0.9);3.137 (0.9); 3.130 (0.9); 3.128 (0.8); 3.118 (0.9); 2.485 (14.4); 2.476(1.1); 2.472 (1.0); 2.469 (1.2); 2.443 (15.8); 2.319 (0.6); 2.095 (0.7);2.080 (10.1); 2.077 (9.8); 2.045 (16.0); 1.548 (45.2); 1.277 (4.8);1.259 (10.1); 1.241 (4.7); 0.008 (1.6); 0.006 (0.6); 0.005 (0.7); 0.004(0.9); 0.000 (49.9); −0.005 (0.7); −0.009 (1.3) 4-495 CH₂OMe SMe CF₃ H¹H-NMR (400.1 MHz, CDCl₃): 7.664 (1.2); 7.644 (1.6); 7.500 (1.3); 7.480(1.0); 7.259 (17.1); 5.017 (5.7); 3.405 (0.4); 3.392 (16.0); 3.353(0.4); 2.593 (0.4); 2.413 (7.7); 2.270 (0.5); 2.269 (0.4); 2.255 (11.1);2.043 (0.6); 1.569 (0.4); 1.432 (3.8); 1.258 (0.4); 0.000 (7.2) 4-496CH₂OMe SCH₂CH₂OMe CF₃ H

TABLE 5 Inventive compounds of the formula (I) in which Q is Q3, W isC—Y, W is C—Y, R is substituted phenyl and R⁸ is chlorine. Table 5contains 454 compounds (5-1 to 5-454) in which X, Y and Z are as definedin examples 1-1 to 1-454 of table 1, and examples cited hereinafter.

Physical data Nr. X Y Z V (¹H-NMR, DMSO-d₆, 400 MHz) 5-451 Me SMe Me H¹H-NMR (400.0 MHz, CDCl₃): 7.350 (1.3); 7.330 (1.5); 7.260 (36.4); 7.87(1.1); 7.067 (0.9); 2.572 (8.2); 2.505 (7.6); 2.099 (16.0); 1.536(12.0); 0.000 (13.0) 5-462 Et SMe Br H 5-466 Et SEt CF₃ H ¹H-NMR (400.0MHz, CDCl₃): 7.628 (3.9); 7.607 (4.8); 7.519 (2.2); 7.469 (3.8); 7.448(2.9); 7.293 (2.3); 7.260 (412.7); 7.225 (0.8); 6.996 (2.2); 3.152(1.7); 3.133 (4.9); 3.115 (5.1); 3.096 (1.7); 2.748 (2.1); 2.729 (6.2);2.710 (6.4); 2.692 (2.1); 1.570 (1.0); 1.537 (164.7); 1.293 (6.9); 1.275(15.5); 1.256 (8.3); 1.252 (9.0); 1.233 (16.0); 1.214 (7.3); 0.899(1.4); 0.882 (3.9); 0.864 (1.6); 0.146 (0.7); 0.033 (1.0); 0.008 (8.6);0.000 (170.3); −0.009 (4.5); −0.150 (0.7) 5-477 Cl CH₂OMe OMe H ¹H-NMR(400.0 MHz, CDCl₃): 7.587 (2.0); 7.565 (2.2); 7.268 (0.5); 7.2673 (0.6);7.2665 (0.7); 7.266 (0.9); 7.265 (1.0); 7.264 (1.3); 7.263 (1.6); 7.259(89.9); 7.256 (1.8); 7.255 (1.2); 7.2543 (0.8); 7.2535 (0.6); 6.816(1.4); 6.794 (1.3); 4.565 (5.0); 3.873 (9.8); 3.324 (16.0); 1.531(10.7); 0.008 (1.1); 0.000 (36.7); −0.009 (1.0) 5-484 Cl[diethyl(oxido)- Cl H ¹H-NMR (400.0 MHz, CDCl₃): lambda⁶- 7.521 (0.6);7.330 (20.6); sulfanylidene]amino 7.320 (0.6); 7.319 (0.6); 7.309(26.0); 7.270 (0.7); 7.262 (100.4); 7.140 (24.3); 7.134 (0.5); 7.119(20.6); 6.998 (0.6); 4.130 (1.3); 4.113 (1.3); 3.281 (0.7); 3.263 (2.2);3.246 (5.4); 3.235 (4.9); 3.227 (15.9); 3.217 (15.5); 3.209 (16.0);3.198 (16.0); 3.190 (5.3); 3.180 (5.7); 3.163 (2.2); 3.145 (0.7); 2.045(6.0); 1.555 (20.5); 1.478 (43.4); 1.460 (97.5); 1.441 (41.6); 1.425(0.7); 1.295 (0.6); 1.277 (2.1); 1.259 (4.5); 1.247 (0.5); 1.241 (1.9);0.008 (1.4); 0.000 (48.1); −0.009 (1.3) 5-485 Cl (4-oxido-1,4lambda⁴- ClH ¹H-NMR (400.0 MHz, CDCl₃): oxathian-4- 7.713 (0.7); 7.692 (0.7); 7.529ylidene)amino (0.8); 7.520 (3.7); 7.508 (0.9); 7.492 (0.6); 7.482 (1.3);7.420 (0.6); 7.390 (1.5); 7.369 (1.0); 7.354 (1.3); 7.349 (1.8); 7.343(47.9); 7.333 (1.4); 7.328 (2.1); 7.322 (57.2); 7.302 (0.5); 7.298(0.6); 7.295 (0.6); 7.291 (0.9); 7.290 (0.9); 7.289 (0.8); 7.2864 (0.9);7.2856 (1.0); 7.285 (1.0); 7.284 (1.1); 7.283 (1.2); 7.2824 (1.3);7.2816 (1.3); 7.281 (1.4); 7.280 (1.4); 7.279 (1.6); 7.2784 (1.7);7.2776 (1.9); 7.277 (2.0); 7.276 (2.2); 7.2752 (2.5); 7.2745 (2.5);7.274 (2.8); 7.273 (3.1); 7.272 (3.4); 7.271 (3.4); 7.2704 (3.8); 7.2696(4.6); 7.269 (5.7); 7.268 (5.8); 7.2673 (6.7); 7.2665 (8.2); 7.266(9.8); 7.265 (12.3); 7.264 (17.0); 7.261 (625.8); 7.256 (6.1); 7.255(3.7); 7.254 (2.7); 7.2534 (2.4); 7.2526 (1.8); 7.252 (1.5); 7.251(1.4); 7.250 (1.1); 7.2494 (0.9); 7.2486 (0.9); 7.248 (1.2); 7.247(0.7); 7.228 (0.6); 7.211 (0.5); 7.173 (0.8); 7.160 (55.2); 7.39 (45.5);7.126 (0.6); 6.997 (3.6); 4.328 (6.6); 4.320 (8.8); 4.314 (7.6); 4.305(7.3); 4.297 (10.0); 4.268 (11.1); 4.282 (13.5); 4.273 (10.5); 4.193(11.4); 4.187 (13.2); 4.172 (12.2); 4.165 (13.1); 4.155 (8.3); 4.149(2.9); 4.140 (8.7); 4.134 (8.2); 4.113 (3.2); 4.095 (1.2); 3.492 (6.3);3.482 (5.6); 3.471 (6.1); 3.460 (11.6); 3.450 (8.6); 3.437 (7.6); 3.429(8.2); 3.364 (1.2); 3.360 (0.9); 3.280 (10.6); 3.272 (11.4); 3.266(10.4); 3.251 (5.2); 3.243 (7.8); 3.237 (8.3); 3.229 (7.5); 2.045(13.8); 1.864 (0.6); 1.545 (157.1); 1.300 (1.2); 1.,277 (5.5); 1.259(16.0); 1.241 (5.7); 1.138 (0.7); 1.085 (0.7); 1.052 (0.6); 0.880 (3.5);0.863 (1.9); 0.853 (2.1); 0.836 (1.5); 0.146 (0.8); 0.000 (282.3);−0.006 (4.3); 0.007 (3.6); −0.008 (8.6); 0.012 (1.7); −0.150 (0.9)

TABLE 6 Inventive compounds of the formula (I) in which Q is Q4, W isC—Y, R is substituted phenyl and R⁹ is methyl. Table 6 contains 454compounds (6- 1 to 6-454) in which X, Y and Z are as defined in examples1-1 to 1-454 of table 1, and examples cited hereinafter.

TABLE 7 Inventive compounds of the formula (I) having 2 identical acylradicals, in which Q is Q1, W is N and R⁶ is methyl.

Physical data (¹H-NMR, No. X Z V DMSO-d₆, 400 MHz) 7-1 F CF₃ H 7-2 ClCF₃ H 7-3 Br CF₃ H 7-4 Me CF₃ H 7-5 CH₂OMe CF₃ H 7-6 CH₂CH₂OCH₂OMe CF₃ H7-7 CH₂-1,2- CF₃ H thiazolidine 1,1- dioxide 7-8 CH₂-pyrrolidin-2- CF₃ Hone 7-9 F F H 7-10 Cl Cl H 7-11 Br Br H 7-12 CF₃ CF₃ H 7-13 F SO₂Me H7-14 Cl SO₂Me H 7-15 Br SO₂Me H 7-16 OMe OMe H

TABLE 8 Inventive compounds of the formula (I) in which Q is Q1, W is Nand R⁶ is ethyl. Table 8 contains 16 compounds (8-1 to 8-16) in which X,Y and Z are as defined in examples 7-1 to 7-16 of table 7.

Physical data No. X Z V (¹H NMR , DMSO-d₆, 400 MHz) 8-16 OMe OMe H 7.91(d, 2H), 6.45 (d, 2H), 4.30 (q, 2H), 3.86 (s, 6H), 3.85 (s, 6H), 1.45(t, 3H)

TABLE 9 Inventive compounds of the formula (I) in which Q is Q2, W isC—Y, R is substituted phenyl and R⁷ is methyl. Table 9 contains 16compounds (9-1 to 9-16) in which X, Y and Z are as defined in examples7-1 to 7-16 of table 7.

TABLE 10 Inventive compounds of the formula (I) in which Q is Q3, W isN, R is substituted phenyl and R⁸ is methyl. Table 10 contains 16compounds (10-1 to 10-16) in which X, Y and Z are as defined in examples7-1 to 7- 16 of table 7.

Physical data No. X Z V (¹H-NMR, DMSO-d₆, 400 MHz) 10-7 CH₂-1,2- CF₃ Hthiazolidine 1,1- dioxide

TABLE 11 Inventive compounds of the formula (I) in which Q is Q3, W isN, R is substituted phenyl and R⁸ is chlorine. Table 11 comprises 16compounds (11-1 to 11-16) in which X, Y and Z are defined in Table 7.

TABLE 12 Inventive compounds of the formula (I) having 2 identical acylradicals, in which Q is Q4, W is N and R⁹ is methyl. Table 12 comprises16 compounds (12-1 to 12-16) in which X, Y and Z are defined in Table 7.

TABLE 13 Inventive compounds of the formula (I) in which Q is Q1, Z ismethylsulfonyl, W is C—H, Z is trifluoromethyl, V is hydrogen and R⁶ ismethyl.

No. R Physical data, (¹H-NMR, DMSO-d₆, 400 MHz) 1 Me 8.36 (s, 1H), 8.26(d, 1H), 8.06 (d, 1H), 4.12 (s, 3H), 3.38 (s, 3H), 2.22 (s, 3H) 2 Et 3i-Pr 4 c-Pr 5 CH₂CHMe₂ 6 CF₃ 7 CH₂CHF₂ 8 CH₂CF₃ 9 CH₂OMe 10 CH₂SMe 11CH₂SO₂Me 12 CH₂CH₂CN 13 CH₂CH₂OMe 14 CH₂CH₂OEt 15 CH₂CH₂OPh 16 CH₂CH₂SMe17 CH₂CH₂S(O)Me 18 CH₂CH₂SO₂Me 19 CH₂C(O)Me 20 CH₂C(O)Ph 21 CH₂CO₂H 22CH₂CO₂Me 23 CH₂CN 24 CH₂C(O)Me 25 CH₂CO₂H 26 CH₂CO₂Me 27 CH₂CH₂CN 28allyl 29 propargyl 30 phenyl 31 4-Cl-phenyl 8.44 (d, 1H), 8.40 (s, 1H),8.31 (d, 1H), 7.63 (d, 2H), 7.52 (d, 2H), 4.22 (s, 3H), 3.41 (s, 3H) 324-OMe-Ph 8.40 (d, 1H), 8.39 (s, 1H), 8.29 (d, 1H), 7.58 (d, 2H), 6.97(d, 2H), 4.20 (s, 3H), 3.79 (s, 3H), 3.41 (s, 3H) 33 pyridin-3-yl 34benzyl

C. BIOLOGICAL EXAMPLES 1. Pre-Emergence Herbicidal Action AgainstHarmful Plants

Seeds of monocotyledonous and dicotyledonous weed plants and crop plantsare laid out in sandy loam in wood-fiber pots and covered with soil. Thecompounds of the invention, formulated in the form of wettable powders(WP) or as emulsion concentrates (EC), are then applied to the surfaceof the covering soil in the form of an aqueous suspension or emulsion ata water application rate equating to 600 to 800 I/ha, with addition of0.2% wetting agent. After the treatment, the pots are placed in agreenhouse and kept under good growth conditions for the trial plants.The damage to the test plants is scored visually after a test period of3 weeks by comparison with untreated controls (herbicidal activity inpercent (%): 100% activity=the plants have died, 0% activity=likecontrol plants). In this case, for example, compound Nos. 1-086, 1-028,1-206, 1-447, 1-448, 1-449, 1-454, 1-458, 1-470, 1-471, 1-472, 1-477,1-487, 2-477, 2-480, 2-500, 3-143, 3-475, 3-491, 4-188, 4-495, 4-430,4-496, 13-001, 13-031 and 13-032, at an application rate of 320 g/ha,each show at least 80% efficacy against Abutilon theophrasti andVeronica persica.

2. Post-Emergence Herbicidal Action Against Harmful Plants

Seeds of monocotyledonous and dicotyledonous weed and crop plants arelaid out in sandy loam soil in wood-fiber pots, covered with soil andcultivated in a greenhouse under good growth conditions. 2 to 3 weeksafter sowing, the test plants are treated at the one-leaf stage. Thecompounds of the invention, formulated in the form of wettable powders(WP) or as emulsion concentrates (EC), are then sprayed onto the greenparts of the plants in the form of an aqueous suspension or emulsion ata water application rate equating to 600 to 800 I/ha, with addition of0.2% wetting agent. After the test plants have been left to stand in thegreenhouse under optimal growth conditions for about 3 weeks, the actionof the preparations is assessed visually in comparison to untreatedcontrols (herbicidal action in percent (%): 100% activity=the plantshave died, 0% activity=like control plants). In this case, for example,compound Nos. 1-028, 1-085, 1-086, 1-206, 1-447, 1-448, 1-449, 1-453,1-457, 1-460, 1-470, 1-471, 1-472, 1-487, 2-500, 3-143, 3-146, 3-487,3-491, 3-492, 4-144, 4-188, 13-001, 13-031 and 13-032, at an applicationrate of 80 g/ha, each show at least 80% efficacy against Abutilontheophrasti and Veronica persica.

1. Acylated N-(1,2,5-oxadiazol-3-yl)-, N-(1,3,4-oxadiazol-2-yl)-,N-(tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxamide, and/or a saltthereof, of formula (I)

in which the symbols and indices are defined as follows: R is hydrogen,(C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl,(C₂-C₆)-alkynyl, (C₃-C₆)-haloalkynyl, (C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, (C₃-C₆)-halocycloalkyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-OCOR¹,(C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-COOR¹, (C₁-C₆)-alkyl-C(O)R¹,(C₁-C₆)-alkyl-CN, (C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂,(C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R²,COOR¹, CON(R¹)₂, or phenyl, heteroaryl, heterocyclyl or benzyl, eachsubstituted by s radicals from the group consisting of X, Y, Z and V, Wis N or CY, X and Z are each independently hydrogen, nitro, halogen,cyano, formyl, thiocyanato, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl,(C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl,(C₃-C₆)-haloalkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-halocycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, (C₃-C₆)-halocycloalkyl-(C₁-C₆)-alkyl,COR¹, OR¹, OCOR¹, OSO₂R², S(O)_(n)R², SO₂OR¹, SO₂N(R¹)₂, NR¹SO₂R²,NR¹COR¹, (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹,(C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-COOR¹,(C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂,(C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R², NR₁R₂, P(O)(OR⁵)₂, orheteroaryl, heterocyclyl or phenyl, each substituted by s radicals fromthe group of methyl, ethyl, methoxy, nitro, trifluoromethyl and halogen,Y is hydrogen, nitro, halogen, cyano, thiocyanato, (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkenyl, halo-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,COR¹, COOR¹, OCOOR¹, NR¹COOR¹, C(O)N(R¹)₂, NR¹C(O)N(R¹)₂, OC(O)N(R¹)₂,C(O)N(R¹)OR¹, NR¹SO₂R², NR¹COR¹, OR¹, OSO₂R², S(O)_(n)R², SO₂OR¹,SO₂N(R¹)₂ (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹,(C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-CO₂R¹,(C₁-C₆)-alkyl-CN, (C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂,(C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R²,N(R¹)₂, P(O)(OR⁵)₂, CH₂P(O)(OR⁵)₂, CH═NOR¹, (C₁-C₆)-alkyl-CH═NOR¹,(C₁-C₆)-alkyl-O—N═C(R¹)₂, (C₁-C₆)-alkylphenyl, (C₁-C₆)-alkylheteroaryl,(C₁-C₆)-alkylheterocyclyl, phenyl, heteroaryl or heterocyclyl, where the6 latter radicals are each substituted by s radicals from the groupconsisting of halogen, nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy,halo-(C₁-C₆)-alkoxy, (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl and cyanomethyl, andwhere heterocyclyl bears n oxo groups, or Y and Z together with the twoatoms to which they are bonded form a 5-, 6- or 7-membered, unsaturated,partly saturated or saturated ring which, as well as carbon atoms, ineach case comprises s nitrogen atoms, n oxygen atoms, n sulfur atoms andn S(O), S(O)₂, C═N—R¹⁷, C(OR¹⁷)₂, C[—O—(CH₂)₂—O—] or C(O) elements asring members, wherein the carbon atoms are substituted by s radicalsfrom the group consisting of halogen, cyano, (C₁-C₆)-alkyl,(C₂-C₁₀)-alkenyl, (C₂-C₁₀)-alkynyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-alkoxy,phenoxy, halo-(C₁-C₆)-alkoxy, (C₃-C₈)-cycloalkyl, (C₂-C₈)-alkoxyalkyland phenyl, wherein the nitrogen atoms are substituted by n radicalsfrom the group consisting of (C₁-C₆)-alkyl and phenyl, and in which theaforementioned phenyl radicals are substituted by s radicals from thegroup consisting of cyano, nitro, halogen, (C₁-C₆)-alkyl,(C₁-C₆)-haloalkyl and (C₁-C₆)-alkoxy, V is hydrogen, nitro, halogen,cyano, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, OR¹, S(O)_(n)R², R¹ ishydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, (C₃-C₆)-halocycloalkyl,(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl,phenyl-(C₁-C₆)-alkyl, heteroaryl, (C₁-C₆)-alkylheteroaryl, heterocyclyl,(C₁-C₆)-alkylheterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,(C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR³-heteroaryl or(C₁-C₆)-alkyl-NR³-heterocyclyl, where the 21 latter radicals aresubstituted by s radicals from the group consisting of cyano, halogen,nitro, thiocyanato, OR³, S(O)_(n)R⁴, N(R³)₂, NR³OR³, COR³, OCOR³, SCOR⁴,NR³COR³, NR³SO₂R⁴, CO₂R³, COSR⁴, CON(R³)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl bears noxo groups, R² is (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, (C₃-C₆)-halocycloalkyl,(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl,phenyl-(C₁-C₆)-alkyl, heteroaryl, (C₁-C₆)-alkylheteroaryl, heterocyclyl,(C₁-C₆)-alkylheterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,(C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR³-heteroaryl,(C₁-C₆)-alkyl-NR³-heterocyclyl, where the 21 latter radicals aresubstituted by s radicals from the group consisting of cyano, halogen,nitro, thiocyanato, OR³, S(O)_(n)R⁴, N(R³)₂, NR³OR³, COR³, OCOR³, SCOR⁴,NR³COR³, NR³SO₂R⁴, CO₂R³, COSR⁴, CON(R³)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl bears noxo groups, R³ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl or (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,R⁴ is (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl or (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, R⁵ is(C₁-C₄)-alkyl, n is 0, 1 or 2, s is 0, 1, 2 or 3, Q is a Q1, Q2, Q3 orQ4 radical

R⁶ and R⁷ are independently (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,halo-(C₂-C₆)-alkynyl, where these 6 aforementioned radicals are eachsubstituted by s radicals from the group consisting of nitro, cyano,SiR¹² ₃, PO(OR¹²)₃, S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy,halo-(C₁-C₆)-alkoxy, N(R¹⁰)₂, COR¹⁰, COOR¹⁰, OCOR¹⁰, OCO₂R¹⁰, NR¹⁰COR¹⁰,NR¹⁰SO₂R¹¹, (C₃-C₆)-cycloalkyl, heteroaryl, heterocyclyl, phenyl,D-heteroaryl, D-heterocyclyl, D-phenyl or D-benzyl, and where the 7latter radicals are substituted by s radicals from the group of methyl,ethyl, methoxy, trifluoromethyl and halogen, and where heterocyclylbears n oxo groups, or R⁶ and R⁷ are each (C₃-C₇)-cycloalkyl,heteroaryl, heterocyclyl or phenyl, each substituted by s radicals fromthe group consisting of halogen, nitro, cyano, (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, S(O)_(n)—(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy and (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, R⁸is hydrogen, (C₁-C₆)-alkyl, (C₃-C₇)-cycloalkyl, halo-(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy, (C₂-C₆)-alkenyl,(C₂-C₆)-alkenyloxy, halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₂-C₆)-alkynyloxy, halo-(C₂-C₆)-alkynyl, cyano, nitro, methylsulfenyl,methylsulfinyl, methylsulfonyl, (C₁-C₆)-alkylcarbonylamino,(C₁-C₆)-alkoxycarbonylamino, benzoylamino, methoxycarbonyl,ethoxycarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, benzoyl,methylcarbonyl, piperidinylcarbonyl, trifluoromethylcarbonyl, halogen,amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl,methoxymethyl, or heteroaryl, heterocyclyl or phenyl, each substitutedby s radicals from the group consisting of methyl, ethyl, methoxy,trifluoromethyl and halogen; R⁹ is hydrogen, (C₁-C₆)-alkyl,R¹³O—(C₁-C₆)-alkyl, CH₂R¹⁴, (C₃-C₇)-cycloalkyl, halo-(C₁-C₆)-alkyl,(C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,halo-(C₂-C₆)-alkynyl, OR¹³, NHR¹³, methoxycarbonyl, ethoxycarbonyl,methoxycarbonylmethyl, ethoxycarbonylmethyl, methylcarbonyl,trifluoromethylcarbonyl, dimethylamino, acetylamino, methylsulfenyl,methylsulfinyl, methylsulfonyl, or heteroaryl, heterocyclyl, benzyl orphenyl, each substituted by s radicals from the group consisting ofhalogen, nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy,halo-(C₁-C₆)-alkoxy and (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, R¹⁰ is hydrogen,(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl or(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl or phenyl, R¹¹ is (C₁-C₆)-alkyl,(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl or phenyl, R¹² is (C₁-C)-alkyl, R¹³ ishydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, (C₃-C₆)-halocycloalkyl,(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl,phenyl-(C₁-C₆)-alkyl, heteroaryl, (C₁-C₆)-alkylheteroaryl, heterocyclyl,(C₁-C₆)-alkylheterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,(C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR¹⁵-heteroaryl or(C₁-C₆)-alkyl-NR¹⁵-heterocyclyl, where the 21 latter radicals aresubstituted by s radicals from the group consisting of cyano, halogen,nitro, thiocyanato, OR¹⁵, S(O)_(n)R¹⁶, N(R¹⁵)₂, NR¹⁵OR¹⁵, COR¹⁵, OCOR¹⁵,SCOR¹⁶, NR¹⁵COR¹⁵, NR¹⁵SO₂R¹⁶, CO₂R¹⁵, COSR¹⁶, CON(R¹⁵)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl bears noxo groups, R¹⁴ is acetoxy, acetamido, N-methylacetamido, benzoyloxy,benzamido, N-methylbenzamido, methoxycarbonyl, ethoxycarbonyl, benzoyl,methylcarbonyl, piperidinylcarbonyl, morpholinylcarbonyl,trifluoromethylcarbonyl, aminocarbonyl, methylaminocarbonyl,dimethylaminocarbonyl, (C₃-C₆)-alkoxy, (C₃-C₆)-cycloalkyl, orheteroaryl, heterocyclyl or phenyl, each substituted by s radicals fromthe group consisting of methyl, ethyl, methoxy, trifluoromethyl andhalogen; R¹⁵ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl or (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,R¹⁶ is (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl, R¹⁷ is(C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy andhalo-(C₁-C₆)-alkoxy, s is 0, 1, 2 or 3, n is 0, 1 or 2, D is O, S, orNR¹¹, with the proviso that V, W, X, Y and Z are not simultaneouslyhydrogen.
 2. Acylated N-(tetrazol-5-yl)- andN-(triazol-5-yl)arylcarboxamide of formula (I) and/or a salt as claimedin claim 1, in which R is hydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl,(C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl,(C₃-C₆)-haloalkynyl, (C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, (C₃-C₆)-halocycloalkyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-OCOR¹,(C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-COOR¹, (C₁-C₆)-alkyl-C(O)R¹,(C₁-C₆)-alkyl-CN, (C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂,(C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R²,COOR¹, CON(R¹)₂, or phenyl, heteroaryl, heterocyclyl or benzyl, eachsubstituted by s radicals from the group consisting of X, Y, Z and V, Wis N or CY, X and Z are each independently hydrogen, halogen,(C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl, (C₃-C₆)-cycloalkyl,(C₃-C₆)-halocycloalkyl, OR¹, S(O)_(n)R², SO₂N(R¹)₂, NR¹SO₂R², NR¹COR¹,(C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, or heteroaryl, heterocyclylor phenyl, each substituted by s radicals from the group of methyl,ethyl, methoxy, nitro, trifluoromethyl and halogen, Y is hydrogen,(C₂-C₆)-alkenyl, COR¹, CO₂R¹, OCO₂R¹, NR¹CO₂R¹, C(O)N(R¹)₂,NR¹C(O)N(R¹)₂, OC(O)N(R¹)₂, C(O)N(R¹)OR¹, NR¹SO₂R², NR¹COR¹, OR¹,S(O)_(n)R², SO₂N(R¹)₂, (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹,(C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-CO₂R¹, (C₁-C₆)-alkyl-CON(R¹)₂,(C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R²,N(R¹)₂, CH═NOR¹, (C₁-C₆)-alkyl-CH═NOR¹, (C₁-C₆)-alkylheteroaryl,(C₁-C₆)-alkylheterocyclyl, heteroaryl or heterocyclyl, where the 4latter radicals are each substituted by s radicals from the groupconsisting of halogen, nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy,halo-(C₁-C₆)-alkoxy, (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl and cyanomethyl, andwhere heterocyclyl bears n oxo groups, V is hydrogen, Cl, OMe, methyl orethyl, R¹ is hydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl,(C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl,(C₂-C₆)-haloalkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl,(C₃-C₆)-halocycloalkyl, (C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl, phenyl-(C₁-C₆)-alkyl,heteroaryl, (C₁-C₆)-alkylheteroaryl, heterocyclyl,(C₁-C₆)-alkylheterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,(C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR³-heteroaryl or(C₁-C₆)-alkyl-NR³-heterocyclyl, where the 21 latter radicals aresubstituted by s radicals from the group consisting of cyano, halogen,nitro, thiocyanato, OR³, S(O)_(n)R⁴, N(R³)₂, NR³OR³, COR³, OCOR³, SCOR⁴,NR³COR³, NR³SO₂R⁴, CO₂R³, COSR⁴, CON(R³)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl bears noxo groups, R² is (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, (C₃-C₆)-halocycloalkyl,(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl,phenyl-(C₁-C₆)-alkyl, heteroaryl, (C₁-C₆)-alkylheteroaryl, heterocyclyl,(C₁-C₆)-alkylheterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,(C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR³-heteroaryl,(C₁-C₆)-alkyl-NR³-heterocyclyl, where the 21 latter radicals aresubstituted by s radicals from the group consisting of cyano, halogen,nitro, thiocyanato, OR³, S(O)_(n)R⁴, N(R³)₂, NR³OR³, COR³, OCOR³, SCOR⁴,NR³COR³, NR³SO₂R⁴, CO₂R³, COSR⁴, CON(R³)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl bears noxo groups, R³ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl or (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,R⁴ is (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl or (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, n is 0, 1 or 2,s is 0, 1, 2 or 3, Q is a Q1, Q2, Q3 or Q4 radical

R⁶ and R⁷ are independently (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₂-C₆)-alkenyl, where these 3 aforementioned radicals are eachsubstituted by s (C₁-C₆)-alkoxy radicals, R⁸ is chlorine, methyl,methoxymethyl, amino or acetylamino, R⁹ is methyl, ethyl, methoxymethylor methoxyethyl.
 3. Acylated N-(1,2,5-oxadiazol-3-yl)-,N-(1,3,4-oxadiazol-2-yl)-, N-(tetrazol-5-yl)- andN-(triazol-5-yl)arylcarboxamide of the formula (I) as claimed in claim1, in which R is methyl, or phenyl substituted in each case by sradicals from the group consisting of X, Y and Z, W is CY, X is F, Cl,Br, methyl, ethyl, cyclopropyl, trifluoromethyl, methoxy, methoxymethyl,methoxyethoxymethyl, SMe or SO₂Me, Z is hydrogen, F, Cl, Br, I, methyl,ethyl, trifluoromethyl, difluoromethyl, pentafluoroethyl, methylsulfonylor ethylsulfonyl, Y is hydrogen, SMe, S(O)Me, SO₂Me, SEt, S(O)Et, SO₂Et,CH₂OMe, CH₂OEt, CH₂OCH₂CF₃, CH₂SMe, CH₂S(O)Me, CH₂SO₂Me, vinyl, C(O)Me,C(O)Et, C(O)cPr, CO₂Me, CHN═OMe, 4,5-dihydro-1,2-oxazol-3-yl,5-methyl-4,5-dihydro-1,2-oxazol-3-yl,5-methyl-4,5-dihydro-1,2-oxazol-3-yl,5-cyanomethyl-4,5-dihydro-1,2-oxazol-3-yl, 4,5-dihydro-1,2-oxazol-5-yl,3-methyl-4,5-dihydro-1,2-oxazol-5-yl, 1H-pyrazol-1-yl,1H-1,2,3-triazol-1-yl, 2H-1,2,3-triazol-2-yl, 1H-1,2,4-triazol-1-yl,pyrolidin-2-on-1-yl, morpholin-3-on-4-yl, OMe, OEt, OnPr, OCH₂cPr,OCH₂CH₂F; OCH₂CH₂OMe or OCH₂CH₂CH₂OMe, V is hydrogen, Q is a Q1, Q2, Q3or Q4 radical

R⁶ is methyl or ethyl, R⁷ is methyl, R⁸ is chlorine or methyl, R⁹ ismethyl, s is 0, 1, 2 or
 3. 4. A herbicidal composition, comprising aherbicidally active content of at least one acylatedN-(1,2,5-oxadiazol-3-yl)-, N-(1,3,4-oxadiazol-2-yl)-, N-(tetrazol-5-yl)-or N-(triazol-5-yl)-aryl carboxamide and/or salt as claimed in claim 1.5. The herbicidal composition as claimed in claim 4 in a mixture withone or more formulation auxiliaries.
 6. The herbicidal composition asclaimed in claim 5, comprising a further herbicide.
 7. A method ofcontrolling one or more unwanted plants, comprising applying aneffective amount of at least one compound of formula (I) and/or salt asclaimed in claim 1 or a herbicidal composition thereof to the plants orto a site of unwanted vegetation.
 8. A product comprising a compound offormula (I) and/or salt as claimed in claim 1 or a herbicidalcomposition thereof for controlling one or more unwanted plants.
 9. Theproduct as claimed in claim 8, wherein the compound of the formula (I)and/or salt is used for controlling one or more unwanted plants in oneor more crops of useful plants.
 10. The product as claimed in claim 9,wherein the useful plants are transgenic useful plants.